Think about what ordinarily happens to you, then make it a little worse (or maybe double), then think about how you would pay for it.

This is huge to us because I'm getting to get started on my dream much, much earlier than I would've been ordinarily and he's getting a huge chunk of his mortgage paid down . 

Maybe focus it on bigger groups such as church groups, or corporate retreats, or Boy Scouts-Girl Scout troop getaways with parents?

Work from home may have people wanting to upsize but those who would be downsizing are staying put because they don't want a bunch of covid possible people trooping through their homes if they are part of a more vulnerable older population.  

This ordinarily wouldn't be a problem since the portfolio loans would work through an LLC, however my fiance and I are looking to purchase a single family home for ourselves within the next year.

I have told the purchaser that I will manage the rental free-of-charge until the end of the year so that we don't have to cancel a bunch of peoples' vacations, but I don't think it ordinarily works that way.  

Ordinarily, you don't want to pay the tenant the same you would an independent contractor because you'll end up in a bind if they do sub-par work, don't finish the job, etc.

You're enabling them to live in something they ordinarily couldn't afford.Rescind the offer.

Ordinarily we would just gut everything in the house and throw it in the dumpster.

I'm also an Eagle Scout and love to give back to my troop.