In my opinion, the best use of your time would be talking with investor-friendly agents and commercial brokers, explaining your criteria and actively following up with them.

I have plenty of friends who make a lot of money off of short term rentals and with the right system it's no more of a pain than long term.

If your "friend" is willing to buy the note at par, then why don't you give him a note and mortgage in return for paying off your existing mortgage... 

Please click on the links, give them a read, and share your thoughts in the comments.First is a post that I feel will help not get overwhelmed with the amount of info that is here on BP:https://www.biggerpockets.com/blogs/5868/52761-the-simple-guide-to-getting-started-on-bpThe second is a post that will help get you focused with your real estate investing goals:https://www.biggerpockets.com/blogs/5868/52743-im-new-to-bp-any-advice-would-be-appriciatedThe last one is a post that will help you choose an “investor friendly” real estate agent.

That's why I work with investor friendly lenders that fund privately and don't require W2s or tax returns (lending based on property not borrower). 

There are tons of posts and articles topics on this, but long story short the Midwest is your friend.

.), Radon, or other environmental issues10. 

(Most "investor friendly" agents actually have minimal experience with investing or investors).

He does wish to purchase his first place to house hack with friends. 

Please click on the links, give them a read, and share your thoughts in the comments.First is a post that I feel will help not get overwhelmed with the amount of info that is here on BP:https://www.biggerpockets.com/blogs/5868/52761-the-simple-guide-to-getting-started-on-bp The second is a post that will help get you focused with your real estate investing goals:https://www.biggerpockets.com/blogs/5868/52743-im-new-to-bp-any-advice-would-be-appriciatedThe last one is a post that will help you choose an “investor friendly” real estate agent.