As far as permits go, I know you don't have to be licensed to pull them (when the last GC I had messed up everything, I removed him from the permits and took them over in my name), but definitely makes sense for the contractor to be on the permit since they will be dealing with the inspector, correct?

Here in Tx when to sell must mention in the seller disclosure if you are aware of more than one layer of shingles installed on the roof...looks like they dont like it for some reason.Check with your agent or with an inspector to know the down side

The inspector dude says it needs a new roof, which in the Pensacola area costs around 8k for a house my size. 

Hi,I need a home inspector for a two flat in Englewood.

Of course the inspector may disagree, so who knows and we'll see.

The inspectors were impressed with his work too. 

Even when I was on layoff I took the national home inspectors exam, passed, and got certified as a housing inspector in Wisconsin. 

Update:According to the inspector, the roof needs to be changed out soon because the shingles are cracked, some spots are showing the foundation that it is glued onto.

And finally, make certain you hire a good inspector - you can try to get credits from the seller (based on repairs the inspector finds) plus it's essential to know what you're getting yourself into, property and repair-wise.

Even after you have an offer accepted you could make 10 calls and find financing, an attorney, an inspector and anyone else you need.