New photos etc.

That average person given limited access to a property is not going to have the experience required to know what to look for.Yes, i would have a couple of your most trustworthy contractors with you when you walk the property and i'd film the walkthrough / take as many photos as you can.With a full hour you can easily assess most of what would be needed to account for 

Ice noticed that Co-living works best when tenants feel respected and connected, which helps with tenant retention and word-of-mouth referrals.

Not sure what the interior will look like, but hopefully you have photos of prior to occupancy, so that you will be able to claim against their security deposit, and a judgement for past due rents and any damages

Hey, I gotta say, I respect your grind.

What are the laws like in Massachusetts with respect to evictions?

You'll need to speak to the building department anyway for permits, so start there with respect to the variance.I'm sorry to say @Jon Pflueger, this is not going to fly.

Are their listings detailed with good-quality photos?

Respectfully, I disagree about the screening process.

We ask for 30 days notice and include that in our lease agreement but understand and are flexible with tenants so long as they are respectful and cooperative.