From what I’ve seen in Bloomberg, it also doesn’t hurt to keep tabs on any shifts in local buying trends.One more thing I’d consider is the exit strategy.

If they’re open to living elsewhere, keeping the property as a short-term rental seems like the more profitable long-term play.If you’re enjoying the self-management and the demand remains strong, I’d lean toward keeping this property as an STR and exploring ways to add another.

With good software available so readily I'd say nah, but you have a partnership with non-family.  

I saw one post where someone mentioned using AppFolio’s bulk upload with a custom spreadsheet, but I imagine there are a lot of different ways people do this.I feel like I might be overcomplicating things, so I’d love to hear how others handle it.

But my gut might be saying no, the following are my thoughts and I'd love feedback:*Not sure a bump from 7 to 9 guests would meaningfully increase nightly rates.

I'd be happy to answer any questions if you think that I can be a resource.

Mid term is primarily what I had in mind: short and event rentals will be more hassle than I'd want to deal with. 

For background, I'm partnered with an architect and interior designer, but I'd have to find most of the subs as I don't have any formal connections (at least in the area I'd like to build).

Sounds like you've been around the block in the RE space before, and I'd love to hear more about your journey chat about what kind of synergistic value we can bring each other.

I'm a commercial mortgage broker and I'd love to connect to discuss debt financing strategies as you come across potential deals.