The Air Force brought me here, and I’ve stayed ever since—I’ve really come to love it here!

I have a feeling just starting out my home is not going to get much exposure on sites like air bnb or vrbo until I get some good reviews.If anyone has experience in this market I would be intrigued to hear how best to manage my new STR.

By house hacking, you're immediately positioned as a landlord, which will adequately pressure you to learn how to structure your leases, screen applications, collect rental payments, resolve the nuances of managing tenants and addressing property issues, etc.

With your background in the Air Force, MBA, and construction, you're in a great position to launch a real estate venture.

The property has forced air furnace in one unit, two boilers heat the other four units. 

No window air conditioners or freezers are ever included in the lease. 

Because they will get defensive if they feel you are pressuring them.

Your income isn't high enough for it to make sense as a rental and the closer you get to your residence limit the greater pressure you will have to sell it before losing your exclusion in whole or part. 500k right now can make $15k per year income with zero maintenance or tenant risks. 

Like others have mentioned, a 30 year loan is better (less pressure).

Almost nobody in the Upper Peninsula has air conditioning though so maybe can save money on just doing a new furnace and not a full HVAC, we'll see.