How I Lost Money in Real Estate Before It Was Fashionable, Part V: Sold! and the Taxman Cometh

Previously:  Part IV:  I Become a Landlord

Part V: Sold! and the taxman cometh.

One of the few good things to come from all this was the bond and friendship we owners developed.

My pal, whose name I have somehow shamefully managed to forget, was now the Condo Association president and he kept an eye on my place for me as it sat empty.  He knew I was desperately interested in selling.  One happy day a woman approached him to ask if he knew of any units available for sale in the building.

“Well,” he said “this is a very desirable building and units rarely come on the market.  But, as luck would have it, I do know one owner who might be persuaded to part with his.”  And he gave her my number.  Bless you and your subtlety, my friend.  I should have remembered your name.

When she called my heart soared with the eagles.  I wasted no time in arranging a business trip to Chicago.

We met. I showed her the apartment. She loved it. (It was, despite the bitter tale surrounding it, quite a nice place.) Turns out her boyfriend lived in the building and they wanted to be closer together. Guess what? His unit and mine shared an adjoining wall. They could, if they so choose, break this wall and create a single grand space.

Not only was this the building she wanted, my apartment was for her the most perfect one. If only she’d been stupid my stars would have been fully aligned. She was not. She was, curse it all, a lawyer.

“How much do you,” she said cooly, “want for the place?”

“Well,” I said as nonchalantly as I could manage, “I hear condo prices have been flat these past few years. I paid $45k for it back in ’79. I could let it go for that.” And then celebrate uncontrollably till my eyes fell out.

“I’ll give you $35k,” she said, not blinking. This is a beautiful moment; when in the course of negotiations you get to a price that works for you and the rest is just how much icing will be on this cake. The weight of years was finally lifting.

A bit of back and forth and we settled on $40k, not coincidentally what I owed the bank.

The deal went through without a hitch. It was the middle of 1985. After six long years I was free and it only cost me $26,960. $5,000 loss on the sale and the $21,960 total of the monthly losses.

Of course, I’d had some tax breaks along the way that softened this a bit, but who’s counting?

The IRS, as it turns out, was counting.

According to them, I had a $15,000 profit and I now owed a $3,000 (20% at the time) capital gains tax on it. Surprised? Well maybe not if you’re one of the real estate pros who read this blog, but I was stunned.

For the rest of us, here’s how.

As I mentioned, with all that cash bleeding away each month, I was desperate for some relief. Turns out when you own investment real estate the acceptable business model allows you to assume the building will wear out over time. This is called “depreciation” and it is considered an operating expense. As such, it is deductible in the eyes of the IRS. Further, back when I was doing this there was an option called “accelerated depreciation” and this is exactly what it sounds like. You can choose to state that your building is wearing out at a faster rate and thereby take a larger deduction. Of course, I grabbed this with both hands like the drowning man I was.

Now here’s the thing. The IRS is nobody’s fool. When you sell they are going to want their cut on your capital gain.  Your capital gain (or loss) is not the difference between what you paid and what you sell it for. It is the difference between your “cost basis” and what you sell it for.

“But wait,” I hear you say, “you sold at a loss, JL. You sold for $40k and you paid $45k. There is no gain to tax.” You are half right. There is no gain, but there is a $15k “profit” to tax. “Cost basis,” you see, is an entirely different thing that what you paid for the place.

The problem is the depreciation I’d been taking must now be accounted for. It amounted to $20k over the years. This $20k reduced my cost basis from the $45k purchase price to an adjusted cost basis of $25k. Since I sold for $40k, voila! A $15k taxable gain.

Here, finally, my sad tale ends. This is the final tally:

  • $21,960 in operating losses
  • $5,000 capital loss on the sale
  • $3000 capital gains tax
  • $29,960 down the tubes

That, my friends, in the early 1980s was serious cash. When I really want to depress myself I calculate that invested in a fund like VTSAX it would be worth around a quarter million dollars by now.

I shoulda bought a Porsche.

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  1. Trisha Ray says

    Jim, We enjoyed the story so much, we’re hardly sorry you went through the experience!
    All’s well that ends well.. and the IRS always seems to win anyway. It’s part of playing the game.

  2. vinoexpressions says

    Interesting to learn about accelerated depreciation, and how it impacts capital gains tax. But finally – you were out. No doubt you were happy to have that anchor no longer weighing you down. And you learned enough (and remember it vividly from quite awhile ago) to steer clear of the same problems in the future. An instructive tale!

    • jlcollinsnh says

      Hi vinoE…

      wish I could have learned that little lesson at less expense. I’d have been drinking better wine sooner.

      Still, it was a great education. Expensive, but great.

  3. Shilpan says

    Jim, I like your candidness. You are a very good story teller. I am sure that this was a roller coaster experience for you, but you learned valuable lessons that you can’t learn from even an Ivy league school. So, it’s not bad. Thanks for sharing.

    • jlcollinsnh says

      Thanks Shilpan….

      …I’ve often thought about the point you make. While it was tough to go thru and 30k expensive there is no better teacher.

      In terms of an education, I got my money’s worth.

  4. Trisha Ray says

    My first house in Spain became a rental house, since I wasn’t there that often. I had a local rental agent. The house was cute, beautiful views of the ocean, and the town was growing. But it really didn’t seem to be doing that well. The agent said it just wasn’t a popular place to rent. Every time I told him I was coming down to visit, the place stood empty.
    One time, without mentioning I was coming, I just flew down for a weekend. Knew it wouldn’t be a problem, since no one ever rented the place anyway. I took my key and opened the door. A shirtless man with a beer in his hand answered. “Who are you?” he asked, somewhat annoyed.
    “Who are YOU?” I asked.
    Well, it of course turns out the place was wildly popular, always full, and always rented. And I never received any of the money. Although I expected the agent to perhaps skim a bit off the top, I hadn’t bargained with receiving absolutely nothing.
    So much for my first rental experience!

    • jlcollinsnh says

      no more than ripping open any long healed scar. 🙂

      Accelerated deprecation was all the RE investment rage back then. Inflation was very high so cash flow was hard to come by and the added deduction helped.

      Price appreciation was the name of the game. You had the unique situation of owning RE assets that were, except for mine, growing in value at the same time you could report to the IRS they were depreciating.

      A beautiful thing right up until you sold.

  5. femmefrugality says

    Holy moly! Learned a lot from this series. That tax thing…I still don’t completely understand it. I mean, I understand it mathematically, but it seems conceptually wrong to me. Leave it to the IRS to rob you…

    • jlcollinsnh says

      Hi FF….

      what a wonderful compliment! You’ve made my day.

      Actually, I’ll defend the IRS on this.

      When the government allows you to depreciate an asset it effectively reduces your tax bill. The idea is that as a cost of business you are using it up.

      When you sell and in fact haven’t actually used it up, it makes sense that they’d want the taxes paid.

      But it is a very painful surprise if you don’t know it’s coming. 🙂

  6. Jana says

    Your story gives me hope (that my husband and I are not the only ones who have made mistakes in this area). I married a wonderful man eleven years ago who was firmly convinced by many in his family that investment real estate was the path to financial security. Instead of selling his little two-bedroom house when we bought a larger home, he wanted to rent it and convinced me –against many exhortations and pleading on my part–to agree to this. I was firmly opposed to the idea but wanted to honor him and figured that he knew exactly what we were getting into. Mistake number one. Mistake number two was refinancing this property at the height of the housing boom here in California. Mistake number three was not selling it in time to avoid capital gains taxes. Now we are paying $300 a month on this property (in addition to our regular mortgage payment) over what the rent brings in. We’re not terribly underwater on this rental compared to many here in CA–we could probably sell it for roughly what it’s worth–but actually can’t afford to sell it right now since we would have to pay $15-20,000 capital gains tax on it. This rental prperty has been the number one cause of anguish and discord in our marriage, and we long to be free of it (my husband now acknowleges that the rental was a bad idea). We are stuck and will need to save for several years simply so that we can pay the capital gains tax and be free of this rental. It was reassuring somehow to read your condo/rental story and to hear that others have made mistakes in this area and have been able to recover from them eventually, with careful saving and frugal living.

    Thanks for your very helpful series of posts on this subject!

    • jlcollinsnh says

      No Jana….

      …you are not alone!

      Rental RE can be a wonderful investment, but it takes careful planning and a lot of work. . sounds like you guys backed into yours like I did mine.

      and, as you well know, it can be very hard to get out from under a bad one. But the nightmare will end.
      You just have aggressively save enough to pay the tax and be done with it.

      The good news is that by the end you’ll have that savings discipline going on and you can then divert it to you F’you money fund. You’ll wind up better off than ever.

      • Jana says


        Thanks so much for your encouragement. You’re right–I’ve become a lean, mean savings machine as a result of all of this. There’s a silver lining to every cloud, and I am not sure I would have learned to live so frugally without this experience, painful as it has been. Please keep sharing your wisdom–it is much appreciated!

    • jlcollinsnh says

      Thanks Anne….

      …glad you found your way here and enjoyed the series. Knowing what NOT to do can be as important as knowing what to do. My RE expertise is weighted to the former. 🙂

  7. Young says

    Dear Jim,

    Two part comment. First, I’d like to thank you for sharing your stories, knowledge and wisdom. I started reading your posts about a month ago after reading your story on MMM. Such a pleasure to read. The path to FI is much clearer to me now thanks to your posts, MMM’s and others’. And I appreciate your gentle (and fun) approach to responding to comments and questions. The way you responded to Paris Parsa’s comments under “Ask jlcollinsnh” (Dec 13, 2013) with kindness and respect stands out in particular for me.

    Second, thank you for this eye-opening series on real estate. I can’t imagine the pain you must have went through. It certainly made an impact on my rosy perception of real estate. My wife and I were pretty well set on renting our former primary residence long term. However, after reading this and re-running the numbers carefully, we will likely change course – to sell it and move the proceeds to a lazy portfolio in a non-retirement account (using the Bogleheads approach as you describe). The kicker for us was the work/time dealing with move-outs / move-ins and learning about the lost opportunity costs – i.e. how the equity could be moved to mutual funds like VTSAX and others. The latter was shrouded in fog for me and is now clear to me (Thank you!).

    In case you and your readers are interested in slightly more detail, the ROI (neglecting depreciation costs) was about 2% per year and the ROI (including depreciation costs) was -3.2%. We anticipate that upon selling, the yearly appreciation rate will amount to about 3% (taking into account compounding over the years we’ve held the property).

    Further, after reading this post, I had a bit of scare and wondered if our yearly losses could be recouped. It seems that they can. According to our tax preparer, the passive activity losses (PALs) incurred over the years can be used to deduct our gains when the property is sold (IRS Code Section 469 PAL

    Thanks again Jim.

    Best Regards,

    • jlcollinsnh says

      Hi Young…

      Thank you so much for your very kind words and I’m very glad to hear you picked up on the “fun” I try to inject into my writing here. Nice to know it works, at least occasionally. 😉

      I had to go looking for that conversation with Paris, it was some time ago! For anyone interested, here’s a link to it:

      One of my goals for this blog is to help others avoid some of the many mistakes I’ve made, so it is is wonderful to know this little series provided some useful perspective for you.

      Unfortunately it came too late for Lina below. Like me she gets the good story and expensive and painful education. 😉

  8. Lina says

    Wow, your entire story parallels my story on so many levels.

    I finally sold the rental property just a couple of months ago after 7 years of nightmarish ownership. I, personally, vow never to own property again. I shall stick with mutual funds.

    Gives me hope that you became so fiscally independent and sage after your experience.

    • jlcollinsnh says

      If that’s the case, my condolences! 🙂

      Glad to hear you’ve unloaded it. Like me, you’ll now have a great story going forward and you’ve had a great, if painful, education. 😉

  9. Booby hatch says

    Sold 2 houses in SF Bay Area, exchanged them for a house in Hawaii. Managing from afar difficult. No renters yet, can’t sell for many years (1031 rules about protecting cap gain from tax), and wondering why I left a lucrative rental market- I’ll be working until I’m 80 because of this fiasco. The only moneymakers are the pool guy, gardener, cleaning lady, insurance agent and Hawaiian utilities. My chance at recovering my fortune will be to rent a tiny apartment there and houseclean before/after vacationers.

  10. JT says

    My dad has similar stories from his forays into landlording in the 1980s. He uses them to try and persuade me away from RE as an asset class, but so far to no avail. I try to tell him that I actually analyze my deals, buy them low, force equity through improvements (done by me), and I screen tenants rather than renting to the first person who calls.

    And any gains (real or imagined) on sale will be 1031 exchanged into another rental property.

    I am positive that I will have some bad deals, potential legal issues, and heartbreak in my investing future, but RE is a critical part of my strategy (and along with being frugal has allowed me to retire at 35).

    Or maybe I’m just young and foolish. I can’t discount that possibility.

    • Dede says

      You could do very well in the Bay Area with your business sense. If I were your age I would have kept my 1031 transaction in the Bay Area. However, life is short so my husband and I bailed from that real estate land of impossible rents and staked our fortune in Hawaii. Tough going but we are having fun!

    • jlcollinsnh says

      Hi JT…

      There is definitely money to be made investing in RE. I went on to do so myself after the debacle described in this series. I may be slow, but I do learn eventually. 🙂

      Eventually, I decided it was too much like work for my tastes.

      But if you are willing to do the work, and keep your wits about you, you can do very well.

      My friend Paula has and excellent blog on this:

      Good luck!

  11. RocDoc says

    We all need to share our loss stories like this too. It makes each of us feel like we’re not the only one whose ever lost money. You tell the story well. Happily you made it through and are living the dream now, wiser I’m sure for the experience.

    • jlcollinsnh says

      Thanks RD…

      …if I know anything about this stuff, it is due mostly to the endless mistakes I’ve made over the years. 😉

  12. Uri says

    Hi Jim, thank you for share your stories. I would like to ask what do you think of a plan B, that I would take in a similar case…(Plan A, was to sell like you did)

    Plan B:

    1) Most of the $21,960 in operating losses, was not really a loss, since you are paying down the principal and interest…
    2) You sold in 1985 for $40,000 probably around 1995 the same house worth $80,000 (with rents around $600/months) and in 2018 $300,000 (with rents around $1000/months)
    3) 40k, owed the bank, in 1985. lets say that until 1995 yo own 30k to the bank.
    You can refinance the house 70% of $80,000 paid the first loan of 30k and you get 26k to invest in the index! and you don’t have to pay the IRS, agent fees or closing cost…
    4) You invest these 26k in 1995 in the index, which in 2018 will worth around $230k
    5) 2018 you will have $230k + $300k (of the property) + all the rents that you collect from 1985 to 2018…

    We can’t change the past, but I have a property with negative cash flow today, and I think that refinancing is a better option than sell…

    Any feedback from Jim or other investors will be appreciated,


  13. Jeff says

    I really enjoyed reading the story. The one factor you’re forgetting in your calculations is the tax breaks you received by depreciating the asset over your time of ownership. Since income tax is typically higher (depending on your other income) you can probably remove the tax bill from the IRS from your calculation.

    Little you can do at this point, but it can help you realize that you aren’t quite out as much as you thought. Not sure if you check this blog anymore as I’m getting to it at such a late date, but thanks again for sharing.

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