Your safest bet is to call the HOA directly on any potential rentals you have.

If no, you'll likely lose money if they do a shoddy job or charge you way more than quoted at first.If the answer to the last 2 questions was "no", then buying a turn key property (or partnering with someone who has more experience} is probably your best bet.

My last combat tour was back in 2006 and internet was available.

Community banks and credit unions may be the best bet, I'd just call around and keep searching on the forums.

Your best bet is using some type of local or regional lender and using a commercial loan where they underwrite your and don’t source the fundsReach out if you want to talk more about it...i spent a lot of time looking into how to make it work for my partner who was in the same boat!

The person whose name this four plex is in is supposedly 81, according to the internet, and I don’t want to hassle her, but I also think this could be a win-win deal.2.

I assume that jumping in is the best bet!

But I would not bet that your STR would not be shut down, as the city started to enforce things and slapping big fines and having the utility companies turn off power and water to properties that were found to be in violation of the STR rental rules. 

@David S.Based on what you wrote, probably syndication deals are your best bet.

I think some of the folks in Maine are making a bet on appreciation.