I'm not the fair housing landlord expert but I'd probably steer away from referring to it as "veteran housing"Either way I can relate to your situation a little because I also own a house that is shared by multiple people.

You'll also need to be listed on more than just Airbnb, and they are the only platform that allows multiple checking accounts listed.

Work Quality:I hired professionals to inspect the work, and they found multiple issues and evidence of negligence in the construction.

Some states like california you can do trust deeds where you break off the loan into multiple pieces.All of these will require significant capital to scale with your own funds. 

I have seen it multiple times. 

As far as I know, I don't think software like Stessa or Baselane can really track anything related to multiple owners/partners. 

January rolled around and we suddenly had multiple offers.

Maybe a corporate group looking to house multiple workers like for construction or power projects. 

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value. 

If there are multiple offers waiving that would help but most homes on the market are not flying off the shelves.