This property will require about $20k in work for a new roof and upgrades.  

The Ohio quad was straight cash, I am looking into finishing the exterior rehab, and upgrading to a nicer quad or maybe even a down payment on a larger apartment complex.

She could have broken the lease legally.

This has broken our issue and as of today we have rid ourselves of tenant issues (knock on wood...).For property maintenance issues, we maintain them at a high level to prevent the calls. 

I have had several toilet flapper issues and old toilets, so rather than rely on old toilets and dumb flappers, I've taken to upgrading the toilets to a newer model. 

I can tell you how I account for these things but I am sure that my method is just one of several solutions that may fit your circumstances.First, repairs fix things that are broken.  

The cost of those windows would never be recouped, and we would never be able to charge more for rent based on that upgrade (tenants don't seem to care about what type of windows are there).I do know that it was going to be REALLY expensive to have someone install the windows, so my husband replaced them all himself, and he doesn't have any experience.

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It was just a big house broken up into 1 bedroom apartments. 

When they go vacant they get broken into just about every time.