I worked largely in the service industry for many years and there are so many things I love about interacting with people on that level.

Hey Bruce, I would recommend keeping the interaction with your guests strictly within the STR platform.

Many of our tenants we literally only interact to renew their lease once a year. 

Again, the BiggerPockets store has some books for this or you can learn by watching podcasts, reading blogs, and interacting on the forum.

About to install an electric heater, I want to minimize interactions though and avoid requesting $  everyday.

I would try to be sympathetic to his problems, while also getting him to move out as soon as possible and with as little interaction with him as possible. 

I also have a couple bird dogs that interact with offmarket sellers all the time...but they've proven unreliable as you can imagine. 

If I had a million dollars I would use $200k to open a margin account at interactive brokers.

It is difficult to quickly turn someone day when you have them right in front you, they are likely to listen a bit more closely and the chances of one of those interactions turning into a transaction are higher. 

My perception, which to you may be "laughable at best" comes from countless thousands of interactions and personal relationships with wholesalers over the last 13 years.