Wouldn't it be easier to just shop around and find your own roofer?

What kind of contractor would do this- roofer, a GC, HVAC?  

A roofer will tell you "I'm sure I can fix the leak.

If so, would this be a question to ask the roofer or a general labor crew?

Sometimes homeowners hire the cheapest roofer they can find and the roofer doesn't know all the little details. 

I thought about posting this in the tax forum but realized this is more along the lines of a general or landlording topic.Do you guys do patch/mend/repairs on a property shorty after escrow to count it as the "cost basis" for the property, or wait a little while (with or without tenants already in place) to do it and just count it as a repair for that year.

I have a rental that suffered some hail damage, I had my roofer (who told me it was hail damaged) and the  insurance adjuster out.  

The roofer is probably right.

I would appreciate any recommendations for roofers/electricians/plumbers/AC.

Our roofer gets a flat pricing discount on all his shingles, like $58 per square for architectural Owens Corning Duration (really cheap price).