appetite for riskYou can absolutely get a job in RE but keep in mind that it is a cyclic industry where you have to be entrepreneurial to survive downturns, especially times like now when a lot of RE firms are 'trimming the fat' (true in general but even more so in RE)If you're dead set on a W-2 in RE with a good (it's relative, compared to tech, W-2's in RE aren't nearly as exciting) salary and stable, try looking at working for a developer maybe as an analyst.

They might ask about ADA compliance, number of parking stalls, designated Handicap parking, do you have grandfathered in fire suppression, etc.  

Will Wall Street sell houses by the dozens/hundreds due to a change in their investment appetite?

Both options you've presented have their own advantages and disadvantages, The decision of which option to choose will depend on your personal financial situation, investment goals, and appetite for risk.

Yes, most people might not have the stomach for it; however, others who have the personality and risk appetite can do this, for sure. 

But I don't want people who believe solely in Cashflow NOW (because you want to buy a property that cashflows immediately as opposed to waiting for a year or two for the Market to drive up the Rental Rates) to suppress voices like mine.

Let me know if you ever find a solution but I have called pretty much every bank in town asking them and the appetite for risk is just not there right now. 

This is also my brothers account, if you want to connect with me faster, I am on Instagram: andrewbtom  In SD there might be a lower appetite for STR arbitrage with the new restrictions.

If you have more of an appetite for bigger returns, work with an agent that sources off-market deals undervalued and add value to them by doing work vs buying something turnkey. 

In my experience, the investors that are best at preserving their capital do the following: develop a plan, understand their risk appetite, and aren’t afraid to admit a mistake.