If you ask the manager to justify a fee and he starts hemming and hawing, move on or require them to remove the fee.

I have been told by a contractor that the foundation of the building is intact, so it does not need to be torn down but requires a "gut renovation down to the studs."

If you meet that requirement, I highly recommend it. 

I would start by finding areas you actually WANT to live and go from there.Picking a place to call home simply because it has a real estate market that you feel will fit your goals is a great way to end up miserable. 

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

This apartment required a cosmetic renovation that is going to run me around $27,000 to redo.

Make sure to get legal advice on what you can and can’t do for bill back and what kind of notice period is required in your state. 

I know they are compensated per unit for the inspection, do you think it would be an issue if I just registered a fifth unit and made sure it met all the requirements?

It’s not the most simple task unfortunately - definitely requires some technical skill.

@Andreas Mathews admirable, but make sure you do some research so you understand what a PM can make.Starting your own PMC business will require 75-150 doors to make a decent living, depending on gross rents and your fee structre.Working for a SFR PMC as a PM, will require a RE license and you usually get paid a percentage of the gross rents the portfolio of owners/properties you manage generates.