Hiring a bookkeeper to watch the income/expenses is like hiring a gardener to tell you how many roof shingles are laying on the ground after a wind storm instead of hiring a roofer to repair the roof.I recommend that you look for a quality property manager who can maintain the properties and help with the bookkeeping.Start by going to www.narpm.org to search their directory of managers.

I sold a beachfront home last year that was ICF constructed in 2000 with a metal roof on concrete pilings and the insurance went up triple what my larger 2019 stick built with shingle roof 6 lots down is. 

BUT, the shingle manufacturer requires a nailable surface, which a rotted wood board is not, so they are required to pay for it under that.

Assphalt shingling, brick foundation with vinyl siding. 

About a month ago I had a contractor replace a roof that got damaged from a storm but when they had the shingles off another storm blew through overnight and blew the tarp off and a lot of water got in the house.

I redid the roof… it’s multicolored… used up shingles I had laying around… but still a new roof.Trying to decide if I should sell it.

If shingles are broken or missing, leaking, rotting, etc, that's a defect.

The roof was so old that most asphalt shingles were down to just the base fiberglass base material.  

I had 2 - 30 yard dumpsters brought in to hall out the plaster and the old roof (which was like 8 layers of shingles).  

Once you remove the shingles, theres a good chance you might need a new layer of OSB.