Because of this landscape, the best solutions for serious RE investors are - believe it or not - are two extremes: either free Excel/GoogleSheets apps or expensive custom system.

To go alllll the way through with it to where a judge actually tells them to move out or else is extreme.

I really like your attitude and strategy about this because you've taken a potentially difficult issue and made it extremely simple.

It would be unfair for me to increase the rent to that extreme.

The most extreme remedy you asked about is rescission - the court undoes the contract and attempts to put each side back to where they were as if neither entered into the contract. 

this deal will go, but I feel like even in a worst case scenario I'm still doing considerably better than if I was renting (albeit with a lower QoL) and I will hopefully have the safety net of appreciation to bail me out if things go extremely poorly.If I wasn't house hacking, I would not be considering properties that do not generate positive cash flow.

In some states they do use it if a new use would create a higher tax base than the current use, however; it is extremely difficult to do that. 

You've gotta have extremely tough skin.

That's an extremely broad question/statement.

That would depend on the agreement (handshake in this case, extremely difficult to substantiate) between the members.