It use to take me and a guy 3 days to do 1 clean up .

I'm trying to understand if we will need a property manager, or instead, just a handy man service, and a cleaning service, and we'll manage the property ourselves.

A tenant that doesn't call in repair orders all the time, keeps the place clean and never wants to leave is MONEY! 

I don't mind charging lower rents (as long as the numbers work with my plans), but am I going to be stuck at today's low income rental rates while regular rental prices skyrocket?

I am not a CPA so I would ask this question ahead of time, but to my understanding a regular investment property does not qualify as active income even if you are self managing.

I would clean it, prime it with high adhesion primer and apply "porch & floor" paint.

What about the ridges and starter courses, just regular shingles or special ones.Any water/freeze protection at the drip edge by both(???)

If your income is low, now may actually be a better time to sell off some Bitcoin, before regular income pushes you into higher tax brackets.

  ( carpet is 4 yrs old so want to do preventive cleaning. no charge to tenant)  Tenant wants to get vinyl wood flooring instead and says she will pay for herse lf.  

This is almost impossible for regular notes, excepting some types of non-performing paper, which has its own issues.I feel that, currently and continuing until things become predictable, that the safest way to do notes is to buy a property at fire sale pricing, raise the price to market or 10% above and create a seller financed note, which, after some seasoning, can currently be sold at a small discount.