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.

Roofer installed a third layer of shingles over two existing layers.

There were probably a half dozen shingles missing.

Splitting profits is far more viable than running out of money & having to sell.Insurance is tough to get if the roof needs obvious repairs & conventional financing is even more difficult unless the repairs are completed or you have the cash in escrow.We just did a roof on an older home (Insurance requirement) & when we got into it we had 3 layers of shingles & some of the rafters were on 34" centers???.

They used the shingle made from a company called IKO. 

I just replaced the roof, so I shouldn't have to worry about that for 50 years (50-year shingle).

The shingles appear to be in good condition however the SFR has a large sagging area in the roof.  

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. 

I'm currently waiting for roofing supplies (metal shingles) to get that replaced.

If you want to get your license, yYes, you have to hang your shingle, so to speak, under a brokerage.