Maybe I'll start just cutting and pasting in a canned response but for now I'm still customizing for the OP

I also have experience managing remodels, contractors, subs etc and have even taken some community college trades courses (framing etc) so I have some basic trades knowledge.

Most commercial yards put a time limit on your rental anyway in order to be able to serve other customers. 

My suggestion, keep the city out of your business as much as possible.Some of my Montgomery subs will work in Tuskegee. 

When talking to a seller, what are good sub-to questions to determine if it’s a really good deal or not.

A lot of people lost their homes to forclosure when the teaser rates of their sub-prime mortages expired and they could not make their payments.

The company is a 1 man guy who subbed some of the work out to a big environmental company, unsure of what exactly.

This way, we can customize it to our needs and preferences.Our goal is to live in one half and rent out the other for about 7-10 years, then move on to building our "dream home."

You could consider acquiring a second mortgage against the dental office to potentially achieve a blended rate of sub 6.00%, depending on the amount owed on the building and the amount you're looking to take out.

They can make money but from what I've seen your more in the customer care and takes more of your time.