It is likely that the contractor just hail mary'd his bid to see if you would bite because he has other work lined up being that the busy season is here in the northeast.  

I have a duplex under contract that recently sustained roof damage from a bad hail storm.

And flippers are usually hailed as heros..

I agree that it's a shame to remove slate though because it's such a beautiful roof surface that is extremely resistant to the rough New England weather: wind, hail, freeze/thaw cycles and even fire resistant which is why it is valuable (that and a new slate roof is ridiculously expensive).

It’s obviously in a distressed position as everyone in town has had their roofs replaced after a recent hail storm and this one hasn’t been attended to a couple years latter now.  

You still want to buy the normal hazard coverages (fire, wind, hail, earthquake, or whatever natural disasters tend to occur in your area.)Another difference is that you probably don't need any loss-of-use coverage (i.e. hotel expenses if your house is damaged.)Most residential providers will have a policy that is tailored more towards rental homes in the way that I describe above.

On top of that, a separate wind and hail policy is required.

I hail from the MF space so I think along those lines.This is a classic mom and pop operation where they are afraid to raise rents or become to friendly with their client and now fall way behind.

@Filmon Haile,Are you comfortable working with your accountant remotely?

Keep it for capital expenditures, future repairs, mortgage payments and make-ready costs while you have turnovers between tenants, insurance deductibles for hail/fire/flooding and the like.