Does it need a roof and new heating system or just paint and flooring. 

Better than underground homes which have issues with moisture etc.

I'm a pretty handy guy but this would be outside of my realm, but my experience helps me understand how much this type of improvement should cost.Improvements: remodel kitchen and bathroom, paint interior, fix exterior scafolding.How should I go about finding a contractor?

In some homes planting the front or placing pots could increase the curb appeal, in others it could be paint or furniture etc.

I renovated the kitchen with paint and cabinets.

It appears to be a means to an end and the path of least resistance (somewhat related to number 1).

Compliance items such as adding smoke detectors, hand rails, fire resistant garage entry-door and new stairs outside.

And while this is normally uber-boring, frankly, it’s been on fire lately (couldn’t resist).

Resist the urge to oversell yourself and your experience.

I have been looking for a General Contractor to handle all the interior work (Painting, murals, furniture, smart door locks).