No point in hypothesizing if they can even purchase. 2) Offer them money to move out.

We presented this seller with a contract-for-deed offer which was accepted after some negotiation. 

House hacking is so smart and you absolutely can offer your room for rent as well.

Also, you may want to consider using a note servicer (in my area many title companies offer this service). 

Some would argue this offers more protection.

Wondering if others have had any mental blocks when making offers on their first property or buying their first property in general.What were they and how did you overcome them?

I've been offered an opportunity to invest in farm land that is adjacent to a successful/proven farming operation.

It also offers a tax deduction and is a homestead protected against most financial issues or non payment under a Chapter 13 law and a rental is basically a debt burden that if you cannot pay or something happens you get evicted.

I wonder if they ever wound up making an offer.

As the local governments struggle to manage tax payer money responsibly, they should really offer incentives to private builders to build "income restricted" at a much lower price. $220-$300/ft for vertical build costs.