Especially with the favorable tax incentives offered to buy and hold real estate vs the ordinary income tax you'll pay on private lending.A 1031 exchange would allow you to indefinitely defer all of the capital gains tax you would have to pay, and instead use it to purchase better performing property/properties.

There are examples of DSTs that included an exit into a REIT that DID NOT ALLOW the investor to do a 1031 exchange.

Most of our money has been invested in the stock market since we moved to the US in 2017, but we are looking to diversify and generate passive, long-term income.

I'm considering selling my rental property in Atlanta to buy additional properties in the Pittsburgh PA area (using 1031 Exchange). 

Under current rules, NOLs can only be carried forward indefinitely (not carried back).Losses from stocks (Schedule D/Form 8949) follow different rules and cannot be mixed with Section 1231 losses.

It would also help if you bring a solid deal to the table in exchange for the learning experience.

Rent exchanged for work is usually a slippery slope in the future.  

I own a business brokerage firm, Stratton Business Brokers, and am a commercial real estate agent at Commercial Market Exchange.

Which will probably wind up in the stock market.  

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