Did you read Lend to Live?

Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

It makes sense for house mates, spouses etc. to be Additional Insured on a renter's Insurance policy if they also live there and keep their stuff there (although I think anyone on the lease is typically covered anyway).

Most of the “deals” have no meat left on bone except for maybe a long term rental hold after repairs.They ironically sponsor a lot of the meet ups I’ve been too here in DFW. of course they do they live and breath on newbies..  

Tenants should be paying the owner.Do you also live in the house?

My son lives 2 hrs away and could check it once in a while but I don't want to put it on him.Are there any sites/groups that have people that would bring their own sheets and towels, clean up afterwards etc...?

@Hugh Horner I live in the village of Catskill.

It will be remote, but since you live there now, you probably already have connections who either already know the house or local friends to find you good people to service things as needed.  

Right now I have two properties live.

Quote from @Kornelius Friske: We have a STR located in peoria AZ. it's 6 beds (garage conversion) and about 3900 sq ft in total. our energy bill last month was $450 and has been hovering in the $350-$450 range since we went live in august.