I also suggest a drive-by so they are not unpleasantly surprised by the neighborhood when they to the showing, and just keep on driving by anonymously as I wait outside.

You might be very surprised to find out what you see.  

I am expecting items to be found even though there is no visible signs of any issues.I will not be surprised if in the near term the prices fall a little.  

You have found a market out-of-state and have talked to an investor-friendly Realtor you met on Facebook that seems to check a lot of boxes for you and your goals.You worry about making a good choice and how to complete your due diligence on this agent and opportunity.All of my out-of-state buyers buy without ever having seen the property in person but I know they will at some point and want them to have a good experience so I frequently do FaceTime walkthroughs with them before buying and use a very comprehensive property inspector to avoid surprises.

Obviously, it wouldn't be a surprise visit if you scheduled it.

If in the rare chance they do allow short term rentals in the HOA rules/regulations and association documents, don't be surprised if they change that ruling after you buy. 

My savings was completely drained from interest payments and surprise costs I had to manage, and lots of little costs that at the outset I believed this guy would cover (100 to mow grass, every two weeks).

We've had guests do exactly that.We do not advertise any of these supplies until our check-in instructions welcome them to use the pantry, and let this be a pleasant surprise to people when they arrive.In theory a guest could clear us out but nobody ever has. 

Before taking out profits, make sure you have enough set aside for unexpected expenses like repairs, vacancies, or larger maintenance issues.

Oh, the surprises that await you. ;-)