Most paint a pretty rosy picture of the outcomes.   

(New roof, paint, etc) and proceeds even if we paid capital gains taxes could pay down other properties debt including adjustable HELOCS which would double our annual income but of course we would lose a door. 1 property is currently vacant and I anticipate at least $10k to refresh including new gutters.

The smell of fresh paint lol, to me nothing says this place is nice and fresh than that.

This includes small painting projects, deck refinishing, fence repairs, landscaping, etc.

I would make the property habitable whatever that might mean fixing plumbing and paint and concurrently I think you have to do lease violations and start eviction.

Fresh paint throughout, minor repairs, updated outlets/switches, backsplash tile in kitchen/bathroom.

People need to see a pallet that they want to paint.

No issues with @Costin I. deciding Steadily wasn't your best fit but you're painting with a very broad brush to say their insurance is only for total losses or that they're systematically over-insuring their properties to keep deductibles high. 

Painting the walls to remove dust, dirt and nicotine marks.

They literally go out of their way to find the smallest chips, screw holes, stains, paint splash, paint bubble, ANYTHING.