A while back I heard a news story about an apartment complex in a neighboring city getting condemned by the city for a bug problem!

How do you go about analyzing large complexes, farmer inns with tiny houses, campgrounds, etc?

Your best turn in spot for that complex if allowed is half way down between the parking spots and roads towards the other two facilities. 

@Art Giacosa What you are proposing is a more complexed entity structure than my past employer who owned a hotel portfolio valued over $1 Billion dollars.

no reason at all to bring this much complexity injust save up until you can both house hack separately

I would buy mutiple just to cash flow in c and d neighborhoods then when i acired enough cash flow i would keep 2 sell the rest and take the majority of cash you were cash flowing and buy in b neigborhoods or look to put a downpayment on a small apt complex

Everything depends on the HOA and what they will allow as far as amount of rentals (within the complex) and the type of rental (LTR, MTR, STR).

The difference is it's super easy to compare gas prices with no education whereas much more difficult for non-professionals who buy a complex policy maybe a couple times in their life, and often have no education in finance, to compare title policies. 

It's a complex route to get the SRO status off the property via a conversion.

Not as many complexities with a few rentals, but there can still be significant issues depending on entity structure - even if they are all "disregarded" entities for federal tax purposes.If your W-2 is your full time gig, and they are all passive long term rentals, there very well could be likely not a lot of active planning to do on the real estate side, outside of getting some general knowledge out there, having some longer term plans, and ensure deductions are being maximized in the isolation of those 5 rentals.