You could be in an expensive market, like LA, but you inherited a property or you got a killer wholesale deal or subject to and the numbers could be very attractive compared to buying off the MLS for full market price in the same market.

Risky too compared to just holding stocks or bonds.I'm not even worth that much money so I have to ask the more experienced and successful investors on this forum: what keeps you going?

Wraps cost more and take longer (legal fees, recording fees, servicing fees, etc) compared to a SubTo.

Basically when you compare Cleveland to Riverside, California most every Cleveland deal will look amazing to you on paper.

When you researched markets like Austin las Vegas Miami, those markets have higher land cost and are more cyclical in nature tend to have larger price swings compared to regions with lower land costs.

In fact, the appraiser may not even appraise it at $280,000 even though the comparables would point to that value all day long.

And lastly, I search FunishedFinder listings nearby, find comparable properties, and track the listed rent for a few months (does it increase, decrease?).

I'm struggling a bit on that comparing the passivity, appreciation, etc

As long as you stay invested and let your hard earned capital continue to grow, you can pick your spots when a real estate opportunity offers outsized returns comparatively to other investments. 

I would say it depends on how well the chunk of cash in your 401k is performing compared to the asset you are acquiring.