Housing is a major item in someone's life, and is a commitment (you're not just leasing a car, or something).  

My wife and I are both working professionals with two young children, so trying to tackle something that makes sense for us from a time commitment perspective is a big consideration.

You may create a profitable real estate portfolio and work toward eventually managing your own syndicate by making thoughtful decisions and remaining committed to your objectives.Note that investing in real estate involves endurance, patience, and a readiness to absorb lessons from both achievements and mistakes.

Scour it for any potential lease violations this person has committed to see if you can evict him.Hire an experienced landlord-tenant attorney ASAP for your protection.If this tenant is unhinged as you present, they will probably retaliate for anything negative you do to them.

Also I would try to account for the summer months and see if they are certain to commit to a 12 month lease.

I'd check the math on this before committing to this plan - it's not as straightforward as it seems when you get into using Bonus Entitlement. 

Get a commitment on move out date and have them sign for that one month extension.   

Recently, I have made the decision to wholeheartedly commit myself to this journey.My current plan is to invest in a multifamily home for house hacking in my local area or perhaps a single-family property with an unattached garage or basement that I can convert into an Additional Dwelling Unit .

“in an effort to prevent our possible future tenants from over committing to a long term financial liability.

Had I committed as little as 45-90 minutes every other day to filling the vacancy, I think this experiment likely could've had a very different outcome.