Hi Tyler -I've "lived" with couples twice before, once in a conventional house hack situation (I lived in one unit of the building, and they lived in another), and once as "roommates" (separate bedrooms but common kitchen/living room).Wasn't an issue at all in the former.In the latter (which, if I understand correctly, is the situation that you're considering), I had a conversation with them up front about intimacy and inclusivity in common spaces.

Fresh paint, floors/carpet, plumbing repairs, electrical repairs, soffit repair, vapor barrier in crawl space, all sorts of stuff!

I know many in this space that do a very good job.

Flooding crawl space.

Their home might be a good deal but their space rent might be too high for the area, forcing them out and making it difficult to sell.

First and foremost, I hope everyone is staying sane and healthy, we may be quarantined for some time but this could be an amazing space to reset, reflect and recharge from the fast paced city life that we have become accustomed to.I hope your employer or clients are understanding and able to keep you employed and in business.

It is a substantial loss as we are unable to fill the airbnb space and the subtenant lease is significantly below market rate.

I have some experience with renting retail space. 

You can certainly fix up your own spaces (I'm personally finishing my own basement); however, there is an opportunity cost associated with DIY work.

Many would pay $4k a month for a shoebox that feels brand new vs a bigger space that is outdated or not too clean.