When you sell make sure you look into a 1031X rather than a regular sale so you can defer the taxes. 

I'd like to set up a meeting on a regular basis to form some community, share what we're up to, and synergize.  

The regular way is not working.How do people pay their contractors from long distance?   

Regular height or high Ceiling.  

In regular times you would be best serving 60 days notice, but it they don't leave, you still have to go through formal eviction proceedings.

I still go by regularly to check everything myself and restock consumables.

If you rent out more than one, regular laws apply.

Some people hate working from home on a regular basis and believe me the boredom, repetitiveness, etc is very annoying.

I realize that it's hard to get something under $100k that would be in an ideal short term rental location but I'm curious if anyone knows if a smaller house in a "regular" neighborhood of Pensacola would have any viability as a short term rental?

We would definitely stay in touch year round and my portfolio would be very actively managed and rebalanced on the regular, as needed.