I wrote a post for the BP blog just today about improving your credit score. 

It would be different if he was a paying tenant who wanted to paint the master bedroom blue instead of the existing white, or who lost his job at a plant and wanted to improve your property for rent. 

Your refi amount back won't be 100% so you'll need to talk to lenders and see what % you can get back and then decide what your improvement will increase appraisal value.

Improvements should be paid off by about 2 years worth of increased rents, based on what I've read.

I have a home improvement business and I work with a few RE investors who have been sort of mentoring me, but their time is limited and I end up doing a lot of research myself.

I think I'm incrementally getting better at it and I have an out of state strategy in place that should help me reach my goals, but I know I can improve on this a lot and so I keep chipping away at it.

First of all, that roof is a capital improvement, not a repair, so hopefully she didn't try to write that off in 2015.  

I am always trying to strive to improve the community I am investing in.  

Add your improvements to that number for the home iteself for your adjusted basis.

Try to be in control of all investments you are responsible for until you can trust somebody else to do your improvements.