For the uncertain future, you might want to keep a couple properties for your kiddos??

I believe you'll be fine as long as theres no HOA or local legislation against STR's.

It should be noted that wholesaling has been regulated pretty strictly in Pennsylvania and wholesalers have to have a real estate license now among other things so there's likely less wholesaling going on in Philadelphia as in other places. https://consolematison.com/2024/06/12/new-legislation-on-res...

Hopefully, new legislation will change things to entice more carriers to the state.I suggest you reach out to your local insurance broker (where you plan to invest) and explain what you are looking for in a rental dwelling policy. 

Level of Review: Projects are required to submit a substantial amount of project specific information as part of both the application review, approval/legislative process and contract reimbursement process.

anti-landlord legislation.

We haven't bought a deal in 2.5 years in large part because I am uncertain about how to underwrite insurance, but it does seem to be plateauing, and maybe some early signs of dropping. 

However, given its design and commercial-like feel—originally built as a retreat center with a strong Japanese influence—I’m uncertain about the best market to target for a sale.I’m hoping that someone in this group might have connections or advice on how to approach selling a property like this.

So if you are still uncertain, could just make a lease with employer and give that employer rights to sublet to the person, thus your lease is with employer and there on hook to you, and they can deal with the person and all that liability. 

However, they already see a possibility to break it after 6 month due to some uncertain moving parts in their life.