@Jared Cheney in addition to the general inspection do an inspection of the HVAC (central heating and air-condition) if maintenance records are not already available.

My point is to make a list - for both properties and run some numbers so that when you talk with him- it is more in global terms such that "Ok, I might pay your price but I was thinking about the furnace, its an older forced air unit and probably is going to need to be replaced in the next couple years (Start with the most obvious and expensive item). 

In WF, the better neighborhoods for investment are in the south, northwest, up by the air force base, and (especially) the southwest. 

@Louie Jhan Centeno Maglaque  Can you do simple repairs like replace a garbage disposer, replace a hot water heater, replace a motor or capacitor in a central air unit? 

Heat and Air Conditioning can be difficult. 

@Jordan ArringtonDid you have any luck finding some eyes on the ground in Portsmouth?

You're not saving money with the 22 year old air conditioner.

After a total rehab on flooring throughout the house, rewiring, new air units, repainting the outside.

Ductwork can be cleaned and sanitized no need to replace.. the coil can be cleaned or replaced and that’s all that’s to that the blower motor in your furnace blow air across your cold coil that’s how you get cold air.

Strong Air BNB market, also a good property for house hacking.