Since you’re considering Midwest markets, I’d highly recommend adding Detroit to your list of cities to research.

However, I’d like to have a space of my own before living with others again (I plan to house hack again with my next property).I’m seeking advice on how to move forward, as I need to consider things like utilities, taxes, landlord/umbrella insurance, and managing the property, especially with someone renting my garage.Specifically, I’m curious about renting out individual rooms and living on my own for a little while.

Quote from @Bob Schulte: I’ve seen plenty of private money lending stories go south, and it’s definitely a topic worth discussing.

Before I continue, I'd like to make it clear that I am not a financial advisor by any means.

I'd assume CA and WA would be similar.  

I'd also tell them if they need to leave before Dec, as long as they provide 30 days' notice, you are fine with it.

First thing I'd do is check comps to get an idea of the demand and rates you can charge for your condo as a MTR.

I realize these are already very good terms, but I thought I'd check what is possible.

I'd recommend reading these articles on BP for answers to all your questions!

However, I’d probably sell and do a 1031 exchange before 27.5 years due to the depreciation write off for the purchase going away.