The “guts” of the house have been replaced in the past ~5 years in preparation to sell the property.

Also, some will do Replacement cost while others only do Actual Cash Value for how they payout on the loss.You should probably seek quotes from an independent agent.

When was the HVAC, hot water heater replaced?

But she had to go buy a new lock set to replace the one that was broken and had to be forcefully removed. 

I stick to tasks I am allowed to do (patch drywall, paint, replace fixtures, flooring, tile, and cabinets) and hire licensed contractors to do the rest.I've noticed only 1 out of 6 licensed contractors I've hired in the past (HVAC / plumber / electrician / roofers) actually pull a building permit for the work they've been hired to do.  

She does most of the painting, cleaning, lock installation, mini blind maintenance and replacement, caulking, cabinet hardware change outs, electrical wire pulling, fence post hole digging, etc.

Was thinking of replacing with a grey roof and maybe paint the brick white or a light grey.

I’m looking for a contractor to fix a plumbing leak and replace a tub and shower surround and likely some sub flooring in a rental unit bathroom.

If it was put in before 1996, chances are that it will need to be replaced at minimum or at least upgraded when you add on to existing or build a new building on the property.

Redo the hardwoods throughout the main floor, paint the whole house, put on new doors, and replace all the light fixtures.