If there were payment issues with the original subs, this becomes even trickier and could result in clouded title with mechanics liens.

Two separate issues: 1) getting tenant to pay whats owed and 2) switiching the bills.1) court and collection followed by eviction process starting.

The only issue is that I don't think I can qualify for the loan I would need to do that.

Plus it becomes a norm for my tenants and they usually anticipate it.Only one tenant gave me an issue this past year and I reassured them that I wouldn't raise their rent anymore than $25/yr.

There were red flags but I had worked with this contractor before and did not have issues.

He has many real estate clients so he knows real estate issues very well. 

Typically, they may be more willing to overlook some issues, like current transitional neighborhood, etc, they sometimes have enough cash and other non-descript income to afford a non-refundable option consideration payment, along with somewhat higher than market rent, which would hopefully cover your holding costs.

I had a similar issue with a tenant.

Some tenants I have gone months without talking to and only talked to them because I haven't heard from them in a while (even though their payments come in electronically with no issue).

Would repairs support demand for rent at increased - considering you already have issues with rent payments on time?