There's clearly a leak from the chimney so the walls and roof will need to be ripped out, roof replaced, all rooms updated.

I've had work done on the building itself (roof repairs) and remodeling work in one of my previously vacant units last year. 

It's an older home and the large items (windows, roof, HVAC) haven't been updated in many, many years so one of those items would put the property in the red fairly quickly.It is not a substitute for a thorough rental analysis.

There was a bad roof leak, so he replaced the roof in 2018, and replaced the rotten wood and ceiling.

For some sweat equity and about $5K in materials I will be able to rent it out for about $550 I would guess.It will need a new roof in the future, but it has a few years. 

I know the utilities for homes can be thru the roof.

You go in check the air filters, check for leaks under the sinks, check the grout in the bathrooms, check how the toilets flush, wash down the outside AC unit, check for water in the water heater pan, etc.   

1)  My quotes for a new asphalt shingle roof range from $4,500 to $5,500.  

It has allowed my savings index to go through the roof while still working a full time job.

(Accouting for vacancy, and repairs bit considering it's a new construction I'd don't think the roof will go out in a year).My dilemma is that I feel the price is on the high side and I also realize I have an appraisal contingency.