Seasoned Investors — How Do You Know When It’s Time to Offload a Property?

Question

I’ve been connecting with a few local investors and noticing that some are starting to reassess their portfolios—especially with the current market conditions.

For those of you who’ve been holding multiple properties, how do you decide which ones to keep vs. sell? Is it cash flow, tenant turnover, maintenance issues, or just gut feeling?

Also curious — is anyone considering offloading any properties in Atlanta, GA ? Not necessarily looking to pitch, just trying to understand what motivates that kind of decision.

Would love to hear your perspective!

Greg Scott · Answer

IMO a real estate investor should be evaluating their portfolio at least quarterly, not just because market conditions change.

There are numerous factors to consider that may cause us to decide to sell an asset.  Here are a few:

- Where are we in the business plan?  If we are near the end, we need to decide if we are going to sell or continue to hold.  If we continue to hold, we may need to recapitalize or refinance to reset the deal.

- What is our return on equity?  If ROE has dropped, can it be fixed by doing a cash-out refi. If it is a situation where NOI has stagnated either because rents are down or costs are up, it may make sense to sell instead.

- Do we still like the market?  Sometimes things change

- Is there a unique selling opportunity?  Sometimes there is chance to ring the cash register before you intended, but it makes sense to sell early.

- Can you achieve better returns elsewhere?  As people progress in their investing careers, often they will see bigger and better deals coming at them.  If you can upgrade your returns by trading in one property for others, that makes sense.

- Do you need the cash?  There could be a lot of reasons someone wants cash. One way is to sell a property.

Becca F. · Answer

Great question. Mine has been maintenance issues specifically with out of state properties (Indianapolis) on what was supposed be "cash flow on paper" Class C type of properties. Paying property managers fees and the convenience fee of having them do repairs, etc. If I was local, I'd go over there and do some of the repairs myself.

I sold one Class C when it was vacant and will plan to exit the other one in the next year or two (has a current tenant). The increasing property taxes each year 17% the last assessment, is another factor. So far tenant is fine, no issues there.

I know this is a RE forum but honestly if I sell my OOS I'd consider using the proceeds to buy S&P500 and not buying another property - far less stress with index funds.

Jules Aton · Answer

Thank you for sharing this. I started with rehabs and rentals in my 20s but had I known then what I know now I would have done the live in flip here and there but would not have held as much RE. I would have made as much money without the work, headaches and tying up funds if my asset allocation (AA) had been skewed more toward VTSAX or SCHB.

The blind enthusiasm that it is super easy to make millions in RE with minimal knowledge, work or money wears me out. This is not passive anything or an easy business. People should be aware RE is a business and many new businesses don't survive. Consider this a learning experience, tuition if you will and if you want to try again I'd stay small, local in good neighborhoods even if they may cost a bit more up front. Depending on your age a strong % of your AA in TSM index fund is an excellent strategy to consider.

Ryan Rominger · Answer

From a management perspective, the decision to hold or sell usually comes down to more than just cash flow. High turnover, ongoing maintenance issues, and how hands-on the property feels day to day can tip the scale.

Some clients keep lower-performing properties if they’re in growth areas, while others sell solid rentals to simplify or reinvest in fewer, better-quality assets. It also depends on your long-term strategy like appreciation, income, or peace of mind.

If a property’s becoming a drain (financially or mentally), that’s usually a strong signal to reallocate. It’s all about running the numbers and being honest about the time and energy it's costing you.

Henry T. · Answer

I've made many great investments in the Seattle area, but things have changed. When the local city council votes in anti-landlord legislation, you sell and leave the area.

Chris Seveney · Answer

We are always evaluating our portfolio and make the decision mostly based on "are there better opportunities or better use of time". Of course if a property is not performing well or is going to need a lot of maintenance in the near future that may move it closer to the list to sell, but if its in an A area then we would keep it.

Renee Adams · Answer

@Greg Scott

Thanks for breaking this down so clearly — this is a really solid framework for evaluating when it might be time to sell. I especially appreciate the point about return on equity and unique selling opportunities; those can sneak up on you if you're not watching closely.

I’m having more convos lately with investors who are in that “should I hold or exit?” phase, especially as they reassess markets or start looking for more passive returns. Out of curiosity, have you ever sold earlier than planned because a better opportunity came up elsewhere? Or ever regretted not selling when the signs were there?

Would love to hear how others here approach that pivot moment.

Seasoned Investors — How Do You Know When It’s Time to Offload a Property?

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