This will let more knowledgeable Americans, even if they aren’t wealthy, participate in private market investments such as pre-IPO, venture capital, hedge funds, or private real estate. that will be a cluster F  in a big way unleash those that cant afford to lose money on the most risky investments and the slickest talking promotors what could possibly go wrong

I currently have 2 properties; one rented in California (losing $200/month) and my primary home in NM.

If there’s one thing I wish someone drilled into me when I was starting out, it’s this:Whoever responds fastest… wins.Almost every time.I didn’t learn that from a study.I learned it from losing deals I should’ve had.I’d call a seller back a few hours later and hear:“Sorry, someone else already came by and we signed with them.”That one hurts.Later on, after tightening up my system, the numbers backed up what I experienced:78% of sellers go with the first person who responds. 

With a property manager, you often lose access to the short-term rental tax loophole, which is one of the major perks of STRs.

And maybe lose other customers/sales. 

If you do the rental you lose the $500,000 avoidance at the end of 5 years unless you’re military.

I'm getting cold feed since I'll have all the skin in the game financially, if something goes south on the flip and he doesn't make enough to pay me back, or we lose money, how will he pay me?.

Assuming your HELOC is against your personal residence, you risk losing your family’s house.

I'd be surprised if they end up losing their deposit. 

Won't that get you sued when the person you sold to on a Wrap loses their house to foreclosure?