Imagine getting individual estimate from plumber, HVAC, drywall, roofer etc.Did I get a less competent inspector? 

During heavy rains, which are common in Florida, tenants almost need to wear waders to get from their cars to their apartments.The roofer does offer financing, but the rates are comparable to what we can obtain elsewhere.

The home has a newer roofer (7 years old), New Furnace (2 years old), Newer Windows, and New Electrical.

Most roofers wouldn't provide a quote until the tree was removed.

If you replace them now, then hopefully less headaches going forward.For example, I had to replace a roof on one of my duplexes, so I asked the roofer for a combo deal on another duplex with an old roof to get a better deal.

Percent of rent is USELESS…If your 2000sf home needs a new roof, the roofer doesn’t care if you’re collecting $800/mo in Detroit or $5,000/mo in California.

I had someone come over and put up a tarp, called to get a temp repair, and will have roofer there today to give a bid on a new roof. 

My roofer could probably beat that price uses 30yr comp shingles. 

In what , is he a roofer ?

Even if he did not use the address as his business address as a roofer he still may/would have this type of materials and trailer needed to do his daily stuff and removing the address as business may not change this fact he would bring home.