Even with the use of contractors, it is work managing the contractors and making various decisions.  2) value adds have risks.  

I imagine your ability to find a buyer to assume your mortgage will be there for a long time, so there's no need to make a decision right now.

Supposedly Don is the only decision maker however you can never talk directly to Don.

A house-hack is 99 times out of a 100 going to be a better financial decision than renting / buying a single family home - focus on finding a property in an area you like that is in general good condition. 

This is my first time considering Section 8 so I’m doing my due diligence in making a decision.

I have quotes from some of the bigger names (Progressive, Farmers, Liberty), but curious if there are any others I should take a look at before making a decision.

Everyone knows it when they see it, and nobody wants to deal with it because you can't tell someone fragile that they are making a wrong real estate decision.

By the end of the rotation, I’ll have some say in where my company places me permanently, and I’d like to make an informed decision that aligns with my real estate goals.

The only thing I would think of is decision making.

Ultimately, a lot of your decision will hinge on your strategy and goals.