Come to find out that guy(dressed in an old sweatsuit and driving a total wrecker of a F150) was a major developer in Boston. 

Dressing very casually and  other things that made me uncomfortable as a guest.

If you live somewhere else the same approach.Before we start looking for types of investment properties, let's look at the types of Cash flow or income from REI.Make a new tab on your excel spreadsheet and add this next session.Monthly Cash Flow- rental incomeAppreciation- value increaseExpense reduction- Prom dresses, high school cars, college and internet. 

Tenant Happy.Landlord sleepy.2 am Fire Dept. calls.Fire at such and such a place.We get dress.

But usually it’s by the post-punk-alt crowd, not 2 well dressed ladies with kids.

For the OP it doesn’t matter the state it doesn’t matter how short her dress is or how much you want to think great thoughts for someone.  

I ended up in a bidding war against, of all people, an elderly man dressed like an extra in Fiddler on the Roof.

Also dress well and of course be polite and if they don't want to talk, don't force it.

  #2 Dress very casually like basic jeans, t-shirt, jacket. #3 Do not try to make friends, instead be cordial and respectful #4 Like Jay Ballman said definitely hire a property manager and never reveal your secret identity as the property owner

If I had to, I would kick all the tennants out, dress up the park, start over and get it filled-up.