I had less than 3 rentals for over 5 years and covered under umbrella insurance, also because I was self managing them and doing have work myself which the LLC won’t really cover against (ie the LLC would be solid but if I personally repair something or do the lease/screening wrong as the property manager they can just sue me directly).

You don't choose when and how repairs are done, you can't choose the contractor and you certainly can't negotiate price.

If so you would likely need to pay the estimated repairs out of pocket and it would increase your cash down for looking at cash on cash return. 

Fellow Illinois landlords and property managers,A year ago I rented a home to two individuals who met most but not all of my minimum requirements.  In order to mitigate risk, I asked that they provide 3 months of secu...

That would be a totally different kind of repairs then if your Flipping it.As for the split of gains I guess 50/50 is fine if you both agree to it. 

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).

Every state is different in their foreclosure laws and procedures. 

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.