Are You Holding Too Long… or Selling Too Soon? Let’s Talk About It.

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Are You Holding Too Long… or Selling Too Soon? Let’s Talk About It.

Chase Calhoun
Property Manager · Little Rock, AR · Member since 2018 · 59 posts · 47 votes

Serious question for the investors here:

How do you decide when to SELL a rental, when to REFI, and when to just HOLD long-term?

This came up in a recent conversation, and the more I talk with newer and experienced investors, the clearer it becomes that most people don’t have an actual framework, they’re just going off emotion, fear, or habit.

Here’s the thinking I shared (and where I’m curious if people agree or disagree):

1. Your GOALS should dictate the decision.
If your aim is 5–10 paid-off rentals for retirement, your strategy should look nothing like someone trying to build a 200-unit portfolio or scale a construction/development company.
Different destination = different playbook.

2. A lot of investors are terrified to sell… and it slows their growth.
I used to be “never sell anything.” Looking back, selling a few assets earlier would have freed up capital to take bigger swings.
Some of my fastest growth moments came after letting go of a property I was emotionally attached to.

3. The old BRRRR-style refi play doesn’t always pencil today.
Higher rates = less cash-out, tighter cash flow, more money trapped in the deal.
Refinancing is still a tool, but not the automatic move it used to be.

4. Holding is still where long-term wealth is built.
But holding blindly, just because “that’s what investors do”, can leave you equity-rich and opportunity-poor.

Here’s the real question:
If you could sell one property today at a strong price, recycle that equity into three better deals, and materially accelerate your growth… would you do it? Or would you hold because “that’s the rule”?

I’m curious where the community stands because I’ve seen:

  • Investors who sell too fast and never build lasting wealth.

  • Investors who NEVER sell and miss huge opportunities.

  • And a small group who navigate the middle really well and scale quickly.

I want to hear from you:

What’s YOUR trigger point for selling?
What makes you refinance?
And what makes you say, “Nope, I’m holding this forever”?

Drop your thoughts below, this is one of the highest-leverage decisions we make as investors, and everyone approaches it differently.

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Kevin PolitePro Member
Investor · Decatur Atlanta, GA · Member since 2011 · 612 posts · 232 votes
10mo

I’ve actually changed directions on this recently.

For years, I was firmly in the "never sell" camp. Then I reached a certain age and realized that didn't really match how I wanted my retirement years to look. I was in the 10-unit SFR group and started selling off, doing my best to manage the tax consequences.

A couple things stood out to me along the way:

  1. CapEx gets real after 10–15 years.
    Mechanical systems age, roofs age, insurance gets stricter (about roofs), and maintenance isn’t theoretical anymore. If you hold long enough, you eventually replace everything. That needs to be part of the math, not an afterthought.

  2. Fully paid-off houses produce cash, but the return on equity is much lower.
    It’s nice to be debt-free, but sometimes the equity can work harder elsewhere. That doesn’t mean selling is always right — just that the opportunity cost should be considered.

I've done some BRRRR, I have my license, I've done flips. The question I asked myself was whether the portfolio alone would fund the lifestyle I wanted. My answer was: maybe — if I combined it with other assets and retirement income. So I began unwinding.

I have one closing in a couple of weeks and three left. I’ll keep evaluating how long I want to hold those. And of course, 1031 just means I’m still in real estate, which matters depending on your goals.

My conclusion: there’s no universal rule. Selling isn’t giving up, and holding isn’t a badge of honor. The best decision is simply the one that aligns with your life, your goals, and your timeline.

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  • David Krulac
    Mechanicsburg, PA · Member since 2013 · 3k+ posts · 2k+ votes
    10mo

    Every year around tax time, when gathering data for filing, we evaluate the performance of every asset held.  We call it "thinning the herd".  Under preforming assets are reviewed to determine if changes can be made to improve their performance. Sometimes changes are difficult to make.  Selling properties sometimes is not strictly financing.  One year we sold two building built in 1890, and exchanged for two building built over a century later.  The newer building had fireplaces, central air and garages, that the older building did not.  We had done extensive remodeling on the old buildings to improve them, but they were still old buildings.  Another year we sold a building that did not have off street parking, everybody has cars often multiples and only street parking made the property harder to rent and harder to keep tenants long term.  Another year we sold properties in a distant town where we only owned two and was off the beaten track from other holdings.  The distance and the lower rent scale there persuaded us to sell.

    We've owned a lot of properties for a long time, as long as 37 years,  

    Currently we are working on another project, selling all townhouses, condos, semi-detached, apartments, vacant land and lots and everything built before year 2000.  We are buying 3 bedroom, 2 bath, 2 car garage detached house built since year 2000.  Yesterday put in an offer on another property that met that criteria, after selling a 3 bedroom 1.5 bah 1 car garage house built in 1956.  So the buy box has drastically changed and we will not be dealing with asbestos, lead based paint, ungrounded electric, aluminum wiring, oil heat, steam heat, old windows, little or no insulation, and other such old building attributes.  Of the first 8 properties we bought 3 were longer than 30 years, the shortest was 17 years and the average ownership over 26 years. All 8 have been sold.  At this point I'm building a longtime, generational portfolio. BTW in 3 states where I am buying I'm in the fastest growing county in the state. To quote Bill Murray, "So I have that going for me."

    1Reply
    • Chase Calhoun
      OP
      Property Manager · Little Rock, AR · Member since 2018 · 59 posts · 47 votes
      10mo
      Quote from @David Krulac:

      Every year around tax time, when gathering data for filing, we evaluate the performance of every asset held.  We call it "thinning the herd".  Under preforming assets are reviewed to determine if changes can be made to improve their performance. Sometimes changes are difficult to make.  Selling properties sometimes is not strictly financing.  One year we sold two building built in 1890, and exchanged for two building built over a century later.  The newer building had fireplaces, central air and garages, that the older building did not.  We had done extensive remodeling on the old buildings to improve them, but they were still old buildings.  Another year we sold a building that did not have off street parking, everybody has cars often multiples and only street parking made the property harder to rent and harder to keep tenants long term.  Another year we sold properties in a distant town where we only owned two and was off the beaten track from other holdings.  The distance and the lower rent scale there persuaded us to sell.

      We've owned a lot of properties for a long time, as long as 37 years,  

      Currently we are working on another project, selling all townhouses, condos, semi-detached, apartments, vacant land and lots and everything built before year 2000.  We are buying 3 bedroom, 2 bath, 2 car garage detached house built since year 2000.  Yesterday put in an offer on another property that met that criteria, after selling a 3 bedroom 1.5 bah 1 car garage house built in 1956.  So the buy box has drastically changed and we will not be dealing with asbestos, lead based paint, ungrounded electric, aluminum wiring, oil heat, steam heat, old windows, little or no insulation, and other such old building attributes.  Of the first 8 properties we bought 3 were longer than 30 years, the shortest was 17 years and the average ownership over 26 years. All 8 have been sold.  At this point I'm building a longtime, generational portfolio. BTW in 3 states where I am buying I'm in the fastest growing county in the state. To quote Bill Murray, "So I have that going for me."


       I love the idea of thinning the heard and only selling the underperforming or least desirable properties.

      1Reply
  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    10mo

    I tend to sell too soon but have also made significant gains in TSM index fund investments with proceeds from selling rentals. The older I get and more money I have the less interested I am in dealing with hassles of rental properties. RE is not my full time gig and take this with a grain of salt in consideration of the fact that I just added another STR. Tally past 5 years sold 3 and purchased 3 but with notable improvements in the overall quality of the products even after taxes and transaction costs.

    0Reply
  • Kevin PolitePro Member
    Investor · Decatur Atlanta, GA · Member since 2011 · 612 posts · 232 votes
    10mo

    I’ve actually changed directions on this recently.

    For years, I was firmly in the "never sell" camp. Then I reached a certain age and realized that didn't really match how I wanted my retirement years to look. I was in the 10-unit SFR group and started selling off, doing my best to manage the tax consequences.

    A couple things stood out to me along the way:

    1. CapEx gets real after 10–15 years.
      Mechanical systems age, roofs age, insurance gets stricter (about roofs), and maintenance isn’t theoretical anymore. If you hold long enough, you eventually replace everything. That needs to be part of the math, not an afterthought.

    2. Fully paid-off houses produce cash, but the return on equity is much lower.
      It’s nice to be debt-free, but sometimes the equity can work harder elsewhere. That doesn’t mean selling is always right — just that the opportunity cost should be considered.

    I've done some BRRRR, I have my license, I've done flips. The question I asked myself was whether the portfolio alone would fund the lifestyle I wanted. My answer was: maybe — if I combined it with other assets and retirement income. So I began unwinding.

    I have one closing in a couple of weeks and three left. I’ll keep evaluating how long I want to hold those. And of course, 1031 just means I’m still in real estate, which matters depending on your goals.

    My conclusion: there’s no universal rule. Selling isn’t giving up, and holding isn’t a badge of honor. The best decision is simply the one that aligns with your life, your goals, and your timeline.

    4Reply
    • Chase Calhoun
      OP
      Property Manager · Little Rock, AR · Member since 2018 · 59 posts · 47 votes
      10mo
      Quote from @Kevin Polite:

      I’ve actually changed directions on this recently.

      For years, I was firmly in the "never sell" camp. Then I reached a certain age and realized that didn't really match how I wanted my retirement years to look. I was in the 10-unit SFR group and started selling off, doing my best to manage the tax consequences.

      A couple things stood out to me along the way:

      1. CapEx gets real after 10–15 years.
        Mechanical systems age, roofs age, insurance gets stricter (about roofs), and maintenance isn’t theoretical anymore. If you hold long enough, you eventually replace everything. That needs to be part of the math, not an afterthought.

      2. Fully paid-off houses produce cash, but the return on equity is much lower.
        It’s nice to be debt-free, but sometimes the equity can work harder elsewhere. That doesn’t mean selling is always right — just that the opportunity cost should be considered.

      I've done some BRRRR, I have my license, I've done flips. The question I asked myself was whether the portfolio alone would fund the lifestyle I wanted. My answer was: maybe — if I combined it with other assets and retirement income. So I began unwinding.

      I have one closing in a couple of weeks and three left. I’ll keep evaluating how long I want to hold those. And of course, 1031 just means I’m still in real estate, which matters depending on your goals.

      My conclusion: there’s no universal rule. Selling isn’t giving up, and holding isn’t a badge of honor. The best decision is simply the one that aligns with your life, your goals, and your timeline.


       Love this, great insight!  Thank you for sharing.

      1Reply
  • Eric Blair
    Member since 2024 · 70 posts · 40 votes
    10mo

    Here is where I am torn on this because I feel like I'm in a completely different world than most other investors

    You say you could sell a property and invest in 3 others? Sure if you live somewhere expensive. So here's my dilemma. I live in central Alabama. I bought a property fully leverage with the VA. So I went in with 0% down at a 2.75% rate. Purchased for $110k. Fast forward to today and it's worth $170k and $95k left on the note. I am passed the capital gain cutoff so taxes will hit hard. So here's my question? What the heck could I do with maybe $55k after selling and taxes? I'm certainly not going to find another property for that pipsqueek money. Even in the stock market that's barely pocket change. Right now the property cash flows double its mortgage. So what does somebody like me do with a property that is no longer really appreciating but won't make much from a sell and will make even less in the stock market than what I cash flow?

    0Reply
    • Chase Calhoun
      OP
      Property Manager · Little Rock, AR · Member since 2018 · 59 posts · 47 votes
      10mo
      Quote from @Eric Blair:

      Here is where I am torn on this because I feel like I'm in a completely different world than most other investors

      You say you could sell a property and invest in 3 others? Sure if you live somewhere expensive. So here's my dilemma. I live in central Alabama. I bought a property fully leverage with the VA. So I went in with 0% down at a 2.75% rate. Purchased for $110k. Fast forward to today and it's worth $170k and $95k left on the note. I am passed the capital gain cutoff so taxes will hit hard. So here's my question? What the heck could I do with maybe $55k after selling and taxes? I'm certainly not going to find another property for that pipsqueek money. Even in the stock market that's barely pocket change. Right now the property cash flows double its mortgage. So what does somebody like me do with a property that is no longer really appreciating but won't make much from a sell and will make even less in the stock market than what I cash flow?


       I think in this situation I would leave as is and just take the cashflow and re invest that.  Maybe re evaluate way down the road when the loan is paid off or close to being paid off but that debt in this market is super valuable, especially with no cash into it.

      0Reply
    • Kevin PolitePro Member
      Investor · Decatur Atlanta, GA · Member since 2011 · 612 posts · 232 votes
      10mo
      Quote from @Eric Blair:

      Here is where I am torn on this because I feel like I'm in a completely different world than most other investors

      You say you could sell a property and invest in 3 others? Sure if you live somewhere expensive. So here's my dilemma. I live in central Alabama. I bought a property fully leverage with the VA. So I went in with 0% down at a 2.75% rate. Purchased for $110k. Fast forward to today and it's worth $170k and $95k left on the note. I am passed the capital gain cutoff so taxes will hit hard. So here's my question? What the heck could I do with maybe $55k after selling and taxes? I'm certainly not going to find another property for that pipsqueek money. Even in the stock market that's barely pocket change. Right now the property cash flows double its mortgage. So what does somebody like me do with a property that is no longer really appreciating but won't make much from a sell and will make even less in the stock market than what I cash flow? You're looking at this the right way, but I think you're focusing on the wrong lever.

      You’re looking at this the right way, but I think you’re focusing on the wrong lever.

      You’ve got a property with a 2.75% mortgage, a tenant paying the note, and solid cash flow. That’s a great asset to own. Selling would give you maybe $55K after taxes… and then what? Put it in the stock market and hope for 7%? Try to find a replacement property in your area and laugh at how far $55K gets you?  I’d keep that house. It’s doing its job.You don’t have to hit home runs in a slow-growth market — you just collect base hits. Let that cheap mortgage continue to print cash for you. That’s a huge advantage none of us will ever see again unless rates fall off a cliff.

      When rates eventually drop, that’s when you get strategic: cash-out refi, pull out $30–50K tax-free, go buy another property when the numbers make sense
      . Your market is a cash flow market, not an appreciation market. So play the game that exists, not the one you wish you were in.   If it’s a good tenant, good cash flow, and low hassle, the most profitable move is usually:
      do nothing, and let time work for you. Hold, don’t sell




      2Reply
    • Eric Blair
      Member since 2024 · 70 posts · 40 votes
      10mo

      @Kevin Polite Thanks for this! That brings some clarity. I constantly see post about selling your house and not letting appreciation sit too long but I guess that doesn't apply to everyone 

      0Reply
    • Eric Blair
      Member since 2024 · 70 posts · 40 votes
      10mo

      @Chase Calhoun This is what I have been doing, but accidentally. I've been so paralyzed with selling or not that I literally haven't done anything. It's been several years now lol. I'll probably keep it since it's not really worth it to sell

      1Reply
  • David Krulac
    Mechanicsburg, PA · Member since 2013 · 3k+ posts · 2k+ votes
    10mo

    @Eric Blair First the house I sold was in PA, not really a high priced state, was $360,000 and the 4 bought through Section 1031 were $1.1million. It was done through below market interest rates fixed. For me if I had 2.75% interest fixed for 30 years, I would do my best not to sell and not to refi, so as to keep that low interest rate in place. I had a 2.875% fixed for 15 years, but sold the property (not the one above) which had a $300K+ gain that was tax free, so I sold but if was 13 years old in a15 year term, so only gave up 2 years of the low interest rate. A relative has a 2.0% interest rate which has 26 years to run. I advised them to never sell, and never refinance. The alternative is to get a HELOC or second mortgage that preserves the first in place. Thanks for your service.

    0Reply
    • Eric Blair
      Member since 2024 · 70 posts · 40 votes
      10mo

      @David Krulac Thanks for the great advice. Luckily the temptation to sell is low because I wouldn't make but maybe $55k, and that doesn't seem worth it. I have 20+ years left on the note and it cash flows well. I'll probably keep it for the forseesble future 

      0Reply
  • Chad S.
    Rochester, MI · Member since 2014 · 88 posts · 50 votes
    10mo

    @Chase Calhoun

    I would be willing to sell and move up to a commercial property and turn it over to a property manager, but the numbers just don't work and I'm approaching retirement. That puts me in the never sell camp I guess.

    0Reply
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