Most places require 40k in reserves to get a 200,000 HML so it would definitely take a while to save that kind of money up.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Good summary of what your market is looking for but as we all know, each market tends to have its "wish / want" items which differ from market to market.Flow is definitely a selling point but make adjustments come with a cost. 

To protect our rights, we would definitely deliver a formal 5 day notice (Wisconsin Legal Blank), but at the same time indicate that we are looking to collaborate to find a solution.

Being "boy wonder" can lead to ego and pride definitely comes before the fall. 2) Irrelevant.

A house hack could definitely be a good first step, allowing you to build wealth while maintaining your lifestyle.

The long term rent can most definitely be considered though for FHA. 

Would definitely recommend reaching out to a couple RE attorneys to chat.

Most of the one bedrooms that I have seen in the area seem to be going for 800-950 so I don't think I would have much of a problem, but I definitely want to be well informed before proceeding with this.

I definitely agree with this statement.