A 3/2 1700 sq ft SFR worth 2 mil in the bay area and a 3/2 1700 sq ft SFR in Indy worth $100K both have the same HVAC and roof costs.  

Roof leaks, attic issues, plumbing issues you have no idea exist. 

Other downsides, heater is oil heat, and no central AC (just small window unit), large yard is very overgrown with Himalayan blackberry bushes, and no garage (converted garage to living room space).Upsides: decent condition wood flooring in bedrooms and about half of the living space area, newer vinyl windows in most of the house, outside siding in great shape, roof looks to be in good shape, and the most important upside is the neighborhood, excellent area.FinancialsThere are already multiple offers on the property and they are accepting offers until Monday morning.  

Aluminum siding, pitched roof (not sure on useful age). wood front porch that needs updating.

A good home inspector will provide a detailed report with pictures of all systems from the roof to the foundation.

If yes,keep it and let the tenant follow their pipe dreams of home ownership somewhere else.Don't make their problems yours.If she needs section 8 to pay her bills,she can't safely finance a stick of gum let alone your property and you'd be headed for a long an expensive foreclosure before long.Now if YOU need to sell because you can't afford to repair it or it will need major repairs like a new roof,appliances,etc. and you haven't been setting aside money every month to pay for them well then that's different.Put it on the Bigger Pockets marketplace and let one of us buy it from you and relieve you of the burden.Good luck.

The total property need a new roof, total rehab to the plumbing and the apartments that are not rented needs a total makeover.  

What is the overall condition of the building, roof etc?

Everything was replaced in the house with exception of the things that were new about 5 years ago including A/C, Plumbing, Electrical Service, and roof...

In general,newer is better.Unless you're talking about historical homes in special historical neighborhoods,a 70 year old home is gonna be worth more than the homes pushing 100 years that are probably long overdue for massive repairs and remodeling (new plumbing,rewire the electrics,new roof,water heaters,etc.