The shorter route can also work but IMO, at a much greater expense to your wallet, your conscious, your "higher self" and your quality of sleep at night.     

@Sherwin Gonzales - Our younger Bay Area FTHB homebuyers tend to be progressive and concerned about (or at least conscious of) gentrification/displacement.

Downside would be that it would require more $$ to flip while renting and I'm trying to be as cash conscious as possible short-term.

We sold in '93 for 305k and today the same house is selling > 1mill.There's all kinds of (social, ecological, edu) reasons why this is so, but in this area it is a given.In prime RE areas, the exit plan is not the issue, but the price of entry is a nightmare.

Property Tax and Insurance RatesBe conscious of the property tax of an area and any required insurance such as flood insurance.

But some of my training is in ecology, so I‘ve looked at climate forecasts for different areas when buying homes (that I might hold for a while) to get a sense of how energy, water, fire, flooding, and insurance could change.

I know in the short term my strategy is the smaller scale rehab, but sub consciously, it's like I always need validation for my decisions.

Short-term renters like that are very review conscious and will hold a good review over you and a bad review can kill you so you have to be like a concierge to succeed against other properties in your area.

I made a conscious choice to turn what could have been a mountain that crushed my desire into a stepping stone that compelled me to learn more and more.

I'm always conscious about the sub-floor and it's imperfections, Metro did a pretty good job at smoothing things out (to a degree).