also open to attorney recs who could help us with this This is pretty common, there would be a loan agreement and then a deed of trust in virginia and a mortgage recorded in florida.

There's a home owners association and condo association that pretty much manage and take care of everything on the outside of the building and common areas.

Is this common for these types of loans?

On the one hand, the mentor courses / boot camps / common advice (including many here on BP) is to just set up an LLC but when I've discussed it with professionals, they argue against it.

This is not very common, but a possible risk.And lastly, I am not an attorney, so confirm all of this with a local real estate attorney as part of your due diligence on property.

This is the common issue with most TICs is that all TIC owners end up signing loans with personal guarantees.

Where right before the sale happens the property is quit claimed into the members personal name as tenants in common.  

The most common pathway from where you're currently at with your property is a cashout refi to stabilize it and to pull out your capital for the next project.

Backstory: two luxury cabins in the Rocky Mountains, each sleep a max of 16 but 8-10 guests is more common.

We may habe high property taxes but our rents are high with increases quite common, and insanely low vacancy rates.