IE. heating system, roof, windows?

New roof?

Simple example: if you need a new roof in 10 years and you know it will be 10k, you know you need to set aside 1,000 per year.

The house is almost finished but won’t qualify for FHA or VA financing due to it still needs a roof.

Framing, roofs, exterior, plumbing, electric, ect. 

I own an older house that's in decent shape but needs some renovations including adding dormer to our attic (or just raise the entire roof possibly depending on expense) to facilitate a closet and more headroom creating an actual bedroom. 

On the side, for the past 12+ years, I've been a hammer-swinger for the two residences I own, doing literally everything except roofing (yep, everything, including plumbing, electrical, ductwork, flooring, demolition, framing, drywall, brick-laying, windows, cabinets...... etc).

Limited is a max of 35k in repairs, nothing structural is allowed to be done (you can replace the roof put in a new kitchen, but you cant repair a foundation or cut a hole for a new window for example).   

I'd have to run sewer and all utilities to it, as well as do a studs down remodel (it actually has good bones and a reletively newer asphalt shingle roof). 

Correction:  Roofing question...strip the old or roll right over with new?