New roof on home and garage, electric update, kitchen, baths, floors, front porch, landscape What made you interested in investing in this type of deal?

It is all coming from our "through the roof" property taxes.Yeesh- forget the respect, I've lived without it.

The same amount should be set aside for capital expenditures (roof, paint, carpet) and you have nothing for that. 

Now I would like to replace the whole roof of the house.

All of a sudden Bldg Insp said we HAD to have 2 stair cases down plus an egress window to the lower flat roof & then install a fire sprinkler system.

But it is responsible that the tenant offers to give you back the apartment, rather than continue to rack up unpaid bills. 

Currently no mortgage on either (I own them free and clear) and both in great shape (we were fortunate to be the beneficiaries to substantial grants that allowed for new roofs, furnaces, upgrades, etc, in 2017).

By trashed, do you mean it is uninhabitable or does it just need some deferred maintenance such as flooring and a roof?

The photos look like the property has been updated and he says he has paper work showing upgraded electrical, hvac, roof, termite letter, etc. 

You are already short $50 per month, so no roof, appliances, hot water heater, hvac, bath and kitchen remodel.