So, if I were to sell it by 2020 (within 3 years of turning it into rental), I pocket the entire capital gains on the property (roughly $65k) but I will instantly lose my $750/monthly cash flow from rent as well as depreciation I each year.

You're not only losing money from cash flow(-), but you're losing potential profits from an investment that wasn't taking away your profits...and your seed money at the same time.Those profitable returns you're losing, is (should be) exponential. 

There is no guarantee the price of the home will sit still so you could gain or lose there too.Just some thoughts.

If the tenant doesn't pay, they can lose their section 8 qualifying status, so there is some outside accountability.Cons - Tenants can be more high-maintenance and you may not be able to be as picky about your tenants.

He got paid what a house in that area would sell for plus what he would lose for seven years in rent.

Don't require the current owner to deliver the unit empty or you may lose the deal.

Gursewak you can make money and lose money either way-singles or multi’s, old and new.

Bad news, for you to get that amazing deal, someone needs to lose out and lose badly.  

If i jump in cold turkey, I may end up losing a lot

The only thing I do is post pics of the rehabs I complete for clients and sometimes rehabs I complete for myself (no one knows the difference of who owns what) on IG, no mention of dollar amounts.I am struggling with the realization that I am losing a lot of friends from college by being very successful but I damn sure am not apologizing for it.