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.

Some properties still have the original Slate Roofs which are costly to replace. 

The biggest challenge was replacing a roof after we were under contract to sell and closing during Covid-19.

Roof, HVAC, Kitchen were all updated as of 2018.

Good afternoon,I found a property with potential, the interior needs painting and carpeting, the exterior will need a siding, possibly a new roof and some curb appeal upgrades.According to Rentometer, $1,600 for rent is average.

This is the list I've got in mind:The plumbing system.The electrical system.The structural condition.The heating and air conditioning systems.The basement and foundation.The roof and attic.Evidence of water penetration or grading issues.Appliances and other general components of the home.MoldNot sure about thesePests such as bugs and wildlife.Environmental issues such as radon, asbestos and lead paint.2.

Roof, HVAC, Kitchen were all updated as of 2018.