thanks for helping justify my decision to stay with Stessa.  

I would guess an older home might be more cost to insure?

I have it narrowed down to two agents, one has more general experience in the area and are part of a large organization.  

Troy helped me identify properties with strong short-term rental potential, and when we found this home in Palm Harbor, we moved quickly to make a competitive offer.

HELOC on the TH you're living in sounds the most doable (banks have more appetite to lend when it's owner occupied).Two cents - HELOCs can be great, but it is still debt and you'll want to make sure your base case expected return makes the juice worth the squeeze.

In the 2024 insurance market, CA is hard to place, so even though you could force them onto a single policy, it may be more economical to keep them separate.I'll send you a note with the carriers who can do this for you.

OK, that makes much more sense...so, if you can get an ARV of $460k, then I suspect you can pull out around $53k once the property is "seasoned" (see image)

why not develop something more proven like hotel on portions of it and make this a larger development and carve out pieces?

We might be able to help you but would need more info. 

I could take look at it for you, and help you understand it if it's a standard lease, no need to pay me, although I am not a lawyer.