The rental condo I owned needed a new roof.

A 1926 building has lead, asbestos, clay pipes/orangeburg, needs roof inspection, heater inspection or HVAC if has such. 

I am however a seasoned sub contractor (over 20 years) specializing in custom works but well versed in all aspects of interior and exterior Carpentry.

The only aspect you commented on was income and she doesn't meet income. 

I think we could save on some of the learning aspects of fixing up a kitchen to improve the rents and see if that’s something we would be interested in doing ourselves or just hiring a contractor.

Mine has roof, floors, hvac, hot water heater, appliances, bath and kitchen remodel.

Put in new roof, HVAC system, fixed, replaced parts, and refinished all of the hardwood floors, new kitchen. all of it, down to the non-existent 2 x 4s (historic fire in the kitchen, walls were cardboard and rolled paper in lots of places, new hickory cabinets, fixed falling in ceiling/roof for breakfast room, fixed foundation issues, new subfloor in living room, dining room, new stairs. 

One thing to make sure of while you are doing the fixes is that things are permitted that need to be (plumbing, electric, structural items, roof) because down the road when you sell your property disclosure may ask if items repairs were permitted.  

If it was your dream home and you only sold really because of fear from a money/being able to afford it standpoint I would have turned an aspect of it into an airbnb and used that income to pay down the principle to lower your payment. 

For considering deals, your buyers are going to want to know stuff like repairs that need to be made, condition of major things such as roof/HVAC/plumbing, property ARV (After Repair Value), a few comparable properties for the ARV you came up with, and plenty of quality pictures of the property.