This way if there’s physical damage by residents the company pays the first $500 to fix it.

No, don't "just start" by going on Zillow and spending tens of thousands of dollars to buy a random property.  

If the lender doesn't care about those two (only found one) then I have to already have an active home loan on a primary residence.

Rent out your current residence.

Financial issues: The condo association has insufficient financial reserves or a high number of residents are delinquent on dues.

My two cents- if you are buying as an investment now and plan to move in within the next year, you'll probably be better off waiting and buying it as a personal residence if your time horizon is less than a year- I don't usually tell people to wait, but you'll have to put more down, pay a higher interest rate and there may be tax libilities in that conversion.

I think you know this but for others books on risk like "Black Swan" or "Fooled by Randomness" by Nassim Taleb are excellent reads.

I live in Puerto Escondido, have been here for 4 years and am just a few months away from my permanent residency.

Windows in random rooms were covered in condensation with no clear explanation. 

The construction business usually did 200-300k/year so it made decent money, but I wrote so much stuff off my effective take home was only like 20-40k/year so I'm looking for a new business that's less insane with random expenses, labor, materials, etc so I can stabalize and pay taxes more...Anyway, will probably end up in some kind of marketing/sales role.