The more you maintain your vacation house, they better you will do.

My uncle personally has a few cash flowing rentals that at the time of purchase he got at a good price before major market changes, and even through the overall loss of value in his doors they still maintain a higher growth potential just with the cities intense influx of people, organizations, sports teams ETC...Hope that's in some way helpful!

So, don't just concentrate on vacation rentals. 

You probably want to keep it clear to avoid excess weight and access to maintain the hot tub.

At the same time, these guys have setup significant infrastructure for maintaining these properties (not just maintenance-wise but what looks to be significant technology investments), will they just dismantle those?

The other typical contender is an LLC, but maintaining that entity is expensive.

Obviously in larger cities like LA & NYC these margins of error are quite small +/- 1% because the government surveys a lot of people from these MSAs since a substantial portion of the American population is concentrated there.

Yes, you are personally liable for personal guarantees, but that does not extend constitute piercing the veil of a corporate entity, at least to loans or leases, that is acceptable practice.Hint:Now that you are a member, you might contact others in the state you may incorporate in, you may find an investor willing to work with you and they may agree to allow you to use their name as a registered agent, there is no liability for such agent except to notify you if the authorities inquire, so a very limited service aspect, so long as you agree to maintain the entity. :) 

I'm trying to select things that don't draw in people who can't pay (like no/low deposit) or things that set up an entitlement mentality or that I might not want to maintain.

So the assumption is not that more is better, you have to cost it out to the development requirements by the size of the project, concentration requirements.