They all use the same shingles and paper, so they should all be the same.

I see so much flowers, seed pods and leaves, they sit on the roof and with the daily rain in South Florida the debris completely carpet that section of the roof in a matter of days, and with the captured moisture it causes the shingle nails to rust a lot quicker over time. 

As a lawyer your time is worth a lot more than you will pay yourself for roofing :)And I sympathize, I won’t even tell you about the stolen copper...the staggeringly drunk guy working 60 feet upGet 3 bids, make sure you compare apples to apples (quality of shingles, gutters etc) and also think about speed.

(roof- composition shingle on ranch, a/c heatpump needs to be installed with current duct work from furance, 1.5 jack and jill bath, kitchen, 2 bedrooms , its defiantly outdated!

I am looking to get the shingles replaced and there are a few spots where the wood underneath needs to be torn out and replaced.

The roof is half new and half 4 layers of shingle.  

I reached out to a local roofing contractor (Supreme Remodeling Inc.) and got a quote that was $15-25K for Asphalt Shingle and $25K and up for Tile for a 1,450 sq.ft SFH.

Typical asphalt shingles...

The may have grandfathered policies, but old wiring like fuse boxes, galvanized pipes, or even Tlock shingles may prevent you from getting insurance or paying for riders or having exclusions.   

He said "older people, widows, folks who moved to Florida, call me back when you're old and sick".Well, we'e now old and sick.Recently, my wife recovered from pesticide poisoning, then had a bout of shingles, and we just happen to have a vacancy.