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Our goals are more long-term (buy and hold) and lean more toward appreciating markets, but are not opposed to more CF markets, if it's the right deal.

@Mateo MonsalvePlus the political climate of that foreign country, squatter issues, local laws, tenant rights, etc.

Buy it right and be an excellent host.

Look for people that have owned for over 10 years, and get it from them off market even at a deep discount and do the work of fixing it up and renting it for higher, or if you want to buy on market I'd definitely recommend offering below asking, as most multifamily that hits the market in these areas are tremendously over priced. 

you left out the biggest factor which is risk.

Sounds like you have the right plan in mind.

If so, then HVAC is probably the right size, but you should contact your inspector and ask the question.

The man currently living there is a retired wheelchair bound vet who always pays on time and so they have never felt right raising the rent as hes only living on his Army paycheck.House 3. rents for $800/m the loan will cost me $14,000 as a down payment and $6,000 closing costs, and should cash flow approx $225/m after mortgage payment are made.House 4. 

Well - sale prices are through the roof right now.