If you don't want the property any more a 1031 is probably your best bet, unless it's got a huge capital gains capture in which case you could just take your tax lumps and collect your funds. 

What Don says captures most deals that ultimately looked to have been undervalued by the market, or current owners, but really were not. 

We have 3 projects going in Loudoun county VA and in my poking around there and looking at product there is some massive townhouse developments there to try to capture the starter or lower priced housing..

Hey Qusai, I see you’re dipping your toes into the world of assignment contract wholesaling, and I’ve got to admit, watching someone from a background in finance tackle this is like seeing a chef turn leftover veggies into a Michelin-worthy salad.

Recommendations for you would be to keep super meticulous records of all the costs you’re putting into the property, so your tax pro can make sure you’re capturing everything 1) correctly and 2) in the most tax advantaged way. 

Or is it better to capture all the rental income while continuing to pay my current rent at $500/month?

The stodgy that most of the investors that I work with use is to make sure that every 1-2 years they look at their portfolio and capture the equity to help grow their wealth.As a benefit for the investors that I work with we have partnered with a company that we met at BPCON that looks at this exact thing.

Does not capture the pain investors are going through and will continue to suffer.

I think comparing to the two-- syndications vs index funds-- is too difficult because of the nature of the specific RE under the syndication versus the broad economy(global and domestic) the index funds capture.

These days, even properties with nice amenities like pools need to go the extra mile to capture attention and bookings.