It never hurts to talk. 

I feel just as uncomfortable cold calling as I do asking someone to have me talk to their friend that owns a house.

When a lease ends they’ll suggest new rents and if the tenant hold be offered a renewal. some will offer to transfer utilities for you when it goes vacant, all should handle the transfer when a tenant moves in  With 10 properties I don’t “talk” to my PM more than 2-3 times a year.

I'd talk to more contractors on how to solve the problem.

One I would recommend that you look at is Ocala.I also talk with the OOS investors that I work with about looking at New construction. 

Once you have ran through about 3 months or so of this and penciled out 50-100 deals for fun, I would talk to a local agent and start the process of looking.

I am talking to my financial advisor, who is an expert in this space to gauge pros and cons. 

One Panhandle County I talked to the tax assessor about this one time and this particular property she said the guy was old and had no money so they felt sorry for him and didn't foreclose until he passed. 

No 'press 1 to talk to our sales team, press 2 to...' sort of thing. 

That would do what you are talking about and more.