Selling Rentals Invest in SP500

What is a DST?
I had to look it up.

A Delaware Statutory Trust (DST) 1031 exchange allows real estate investors to defer capital gains taxes by investing sale proceeds into passive, fractional ownership of institutional-grade properties. It meets IRS "like-kind" requirements, offering diversification, passive income (typically 4%-6%), and no management hassle, usually requiring a minimum $100k investment. [1, 2, 3, 4, 5]
 
I don't think it's fair to compare pre-digital age crashes to modern events.

in the early 2000s, trading was hard. platforms to do it were rare.
there were way less folks in the retail investment side as most 'people' were in it only in their mutual funds from a retirement account.
it was expensive to trade (20 bucks a pop to buy, even more to sell with fees added)
social media didn't exist. you had to wait for the editor to approve the article hours after the event.
ai didn't exist

The same can't be said today.
its free, at everyone's finger tips, and even the most non-savvy money folks are able to own and trade with ease for free (eg, the meme stock/robinhood crowd)
information is nearly real time as it happens.


TLDR: it's easier to be more volatile today.

On topic, I sold a rental a while ago when it got to be a pain to manage as it was an hour away. we took about 100k from that as profit and put about 80k into cash holdings/cds/etc and 20k into vti and similar broad growth funds. The 80k is 85k now. the 20k is 90k now.
YRMV

we didn't have a large emergency fund so this was a planned approach, but hindsight is that we didn't need the money (luckily) and lost out on growth of it. such is the price of piece of mind.
 
I have two rental properties I'm planning on selling. I'm anticipating after taxes realtor fees to profit about $250,000 let's just say, but I keep hearing. My concern here is that I keep hearing that the stock market is overpriced and it makes me wonder if investing now is going to be like investing in 1999.

I don't need to touch the money for 25 years. And would want to put more in each year of variable amounts. Might be only $15,000 for a few years per year for that. Maybe it would be more.

What do you guys think I should do
First off, congratulations on putting yourself in a position to walk away with a $250,000 profit.
Your big upside is the 25 years you got there. If you dumped your entire sum into the S&P 500 at the absolute peak of the Dot-Com bubble in 2000, your money would have still roughly quadrupled in 25 years.
 
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