My initial rehab process was I did a number of repairs myself, and then sought out a contractor for the specific task I wanted to hire out (ie Robert @ Southern OR Wood Floors does fantastic hardwood refinishing).

It will convert pictures of paper invoices or whatever into PDFs on the fly wherever you are and you can email them to yourself, then either put them in an email folder for each property, or what I do, download them from email and save them in dropbox (I prefer this over google drive) which uses normal windows folder, and organize digital folders for each property and have subfolders for insurance, loans, tenants, appliances, repairs, you name it.

The only issues were that the 4 older buildings are going to need a new roof at some point during my ownership and the parking lot needed to be repaired. 

I've already got connections for plumbing and electrical, and I can do general repairs that don't require an inspection.

Repairs are the big unknown, You'll have an inspection done to tell you if there are any lurking issues.

The property needs repairs so it would be better if I could have less in to put more towards repairs.2.

Repairs are 36k or likely 45k if I have to convert from well water to county water (I'm noticing that the well is on the edge of the rear boundary, which could be a problem in future).

They will come up with an estimate to do the repairs. 

Even when they tell you that the property is sold, continue analyzing and find out whether you would really pay asking price after knowing all the financials, recent repairs, board of association, recent changes in regulations, etc.

Data:Initial cost = $500/yearService calls = $75/eachAssume, the rent on the property is $1,200/month and a 5% repair reserve ($1,200*12*0.05) = $720/yearUnder this scenario, it tells me the breakeven is about three (3) service calls per year with the warranty company.