[Leah]

Those that used to have rentals and sold, and invested money in stocks instead, how is it going? Any regrets or non at all?

As an investor, I’m curious about your experiences with changes in the stock market over the years.

How has your investment strategy evolved with market fluctuations, and what have been the most significant lessons you’ve learned?

Have you shifted your focus from one type of investment to another (e.g., from individual stocks to ETFs or index funds)?

What factors influenced your decisions, and how have these changes impacted your overall financial goals?

I’m eager to hear about your journey and the insights you’ve gained along the way.

Have you experienced any regrets, or has it been a positive change overall? Your insights and experiences would be greatly appreciated!

[Charlotte]

Everyone is different but we sold our two STRs last year, knowing we’d have capital gains to pay.

I don’t think I can accurately describe how much relief I felt and still feel, knowing that they are gone.

We used the after-tax proceeds to invest AND fill all of our cash buckets for travel, gifts, charity, etc and I have my freedom back.

A gazillion percent worth it (for me).

[Ess]

Aside from owning a rental home, would you recommend anything else best to ease your tax bill?

My accountant says a rental is good for tax breaks but I too don’t want the headaches

[Joe]

What about the depreciation recapture and capital gains etc?

[Jen]

I was definitely not made to be a landlord. I had a rental house for 7 years, sold it, made a pretty large profit in the post COVID market of 2021, and immediately put about 60% of what I made into refinancing my own home to pay it down faster and the rest in a HYSA or an index fund.

I took years off of my own home payments and fast tracked retirement and never looked back.

You don’t have to answer to renters or maintenance calls or give someone else some of your profit if you outsource those things. Just all money to make

Sometimes I get into the trap of seeing other people with rental portfolios and think… “did I make a mistake…?”

And then I look at how much less I owe on my home, how much money I’m still making with the HYSA and index funds and think about how much more time and less headache I have.

Worth it for me personally! But.. I get it that people really like it and do well.

To that I say- good for them, just not for me

PS – I had great renters who found their own replacements when they moved out, all took care of the home, etc.

that was never the problem. Still just didn’t like the nerves & unknowns of being responsible for two properties.

[Yujin]

Zero regrets. Moved a lot of my money into REITs and couldn’t be happier.

No tenants wrecking the place, no PMs nickle and diming me, no problems whatsoever.

My new motto is:

Own your home, invest in REITs and Syndications for real estate exposure.

[Hariprasad]

Looks like most them made good profit from owning rentals. Would you have made that profit elsewhere while borrowing money from banks is the question…

[Dan]

I haven’t retired yet, but I have 7 rentals.
My only regret is not buying more.

Once I bought the last several, my life became easier.

Cash flow, net worth increased, taxes are better.

Yes you have repairs but having good property management is key

[Tony]

Best decision we’ve made! Kids are 10 and 11. Getting our time (summer weekends)back with my family without the tenant calls or todo list has been everything.

We no longer have anxiety or stress hanging over us as well.

We had 15 doors for about 6 years, self managed.

Put 80% of the proceeds into a low cost index fund and it’s been fun watching it grow without having to do anything.

[David]

I did the exact opposite. I sold all my stocks and cashed out all my retirement accounts, 401k, IRAs, HSAs, etc.

(paid the taxes and fees) and purchased rental properties.

My return has been about 14x the s&p.

Given this gain, no amount of difficult tenants or complaints would make it so I would go back into the stock market.

Taking a few calls in the middle of the night is well worth the oversize return.

[Tam]

I would love to get out but my cashflow has allowed me to FIRE 20 years early and I dont know of anything else I will get as much cashflow with before I am retirement age.

[Jule]

We had a rental home for three years, got out of it with 0 regrets. We sleep better at night without tenants and our investments are still growing and doing well.

We were almost at $3M before the latest downturn.

Hopefully the stock market will recover by the end of the year and surpass our 2024 financial goals.

[Elle]

I sold my rentals over the last couple of years, and have no regrets. I feel like I sold when the real estate market was high so I made a decent profit.

Maybe they would sell for more today than when I sold.

But I invested that money and have made as much or more in the stock market.

And my money is more liquid now.

Totally worth it for me.

[Ken]

Not in the same boat, currently renting out my first purchase. Tenants have been relatively easy to work with, I outsourced it to PM.

But am facing a decision to replace my roof for $10+K.

This has been a known issue since I bought it pre Covid.

HVAC will likely be the next big expense.

In all honesty, those tenant helped shaved like $30K off my principal, so it’s been helpful

[Author]

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