Given these circumstances, do you think house hacking in San Diego is still a wise investment for me?

@John Michael RobersonI agree with @Kory Reynolds: tax-wise, it is a workable plan, as long as you are hands-off, which in technical terms is known as failing material participation.I would caution however against focusing strictly on taxes.

Smart investors increase earnings, reduce expenses, increase savings, and buy wisely.

@Roque MirandaI do not but it may be wise to have a lawyer draft one up.

Then half of those don't probably don't make sense ROI wise for most people, and maybe 1/2 of what's left you can rule out due to location or some other factor.#4 While I am sure there are plenty of people that do it, the worst situations I see are investing with friends. 

@Annwar Zahrieh There are certain transactional costs/ costs of doing business in Philadelphia to be mindful of, but I believe the fundamentals that exist in Philadelphia far outweigh this IF investing wisely.

Each individual mountain town also seems to have more strict STR fees than other areas I've looked into.I know you already said you wanted to avoid CO, but just reiterating that it's probably wise to look elsewhere. 

@David Yee you maximize your cashflow in real estate by wisely leveraging your cash.Also, real estate investing is rarely all about the cashflow.

What @James Wise said.

Real estate investments can be very capital intensive, so it is wise to have a strong foundation before diving into your first property.