She's very affable yet effective, the former quality tough to find in an attorney. 

I have learned that it may be beneficial to itemize everything carefully with quality bookkeeping.

Im hoping I can get enough rental income on the first year to cover all expenses including mortgage, cap ex, repairs, vacancy, and hopefully I can wiggle in management for the convenience of properly screening of quality tenants.

Just want to think about characteristics/qualities/etc. that make a good contractor/realtor/etc. 

Therefore hopefully a quality roofer will be able to take me through the process. 

I'm leaving allot of money on the table monthly and annually, but if I try to recapture the lost dollars too quickly I expect I'll  be forcing out quality tenants and face updating costs and vacancy. 

I dunno....getting rid of modest cash flow homes/condos in a blue chip market like SD, and exchanging them for a whole bunch of B and C quality doors in a fly over state = a recipe for disaster IMO.

Based on that number, looks like just over $80K would not be too much for a rehabber to ask and, depending on the quality of the job, might get a little more.

I also like the personable picture of you and your dog (maybe a professional quality one of the two of you would be great). 

If they are quality tenants I would try working with them with possible incremental increases as well if time is not an issue.