I'll be going with an FHA loan, so putting little down would still be possible on these more expensive homes, but how do other investors in Westchester (or in other similar markets) know when they're getting into that "danger zone." 

They tend to be older, have more money and leave the places cleaner.The difference in the 2 platforms is also distinct.

Phoenix is way too expensive (I live at 37th st and IS) and with a  market crash (stock and probably everything else) in 6-8 months a distinct possibility no way would I buy in bubble 2.0 Phoenix land! 

Here is what I found: According to state laws (Civil Code § 1941.1 and § 1941.3), at minimum every rental must have:-effective waterproofing and weather protection of roof and exterior walls, including unbroken windows and doors-functioning plumbing, heating, and electrical facilities, including hot and cold running water and a working toilet and kitchen sink-clean and sanitary building and grounds (that is, free of debris, filth, rubbish, garbage, rodents, and vermin), with adequate trash receptacles-well-maintained floors, stairways, and railings-deadbolt locks on certain doors and windows-no lead paint hazards, and-no nuisances, a catchall provision referring to something that is dangerous to human life, detrimental to health, or morally offensive and obnoxious, such as allowing drug dealing on the premises.If I were you I would take LOTS of pictures and document everything.

The OP distinctly separated AIR and VRBO.

I've never had an issue like this but it sounds dangerous.

Therefore, I would recommend separate LLCs for each distinct partnership or business.

(You would be surprised).2) What if 2 years into renting, "COVID" happens again and the owner takes back his promise because he is getting outrageously high offers on his house and does not want to sell to you anymore. 3) I am sure there are many other "fine print" reasons why this could be dangerous, so my advice is to just save up a down payment or figure out a way to get the title in your name so that you own the house completely.Great Question! 

 I personally would not walk to stadiums from that location.There is always a crowd walking around there who knows why :D)) and it is always a potential danger when house sits vacant.There will be evictions, you should consider that in your calculations.

As Stetson mentions, there does seem to be a distinct high and low season.