My attorney has advised me a structure where: I own the Living Trust --> Living Trust owns the LLC --> LLC owns the property (Title)My lender is not okay with this 'Nesting' arrangement.

Consider a Lease Addendum: If the tenant is willing to comply but you want to formalize the arrangement, consider adding an addendum to the lease that outlines guest policies and consequences for violations.

Are there any potential liability issues that may arise from this arrangement?

Are there any verbal agreements or arrangements between the current Landlord and Tenant?

If you plan to keep, what arrangement does the caretaker have in place? 

For showing they would email a code to lockbox to prospective tenant once the showing appt arranged.

My partner has this arrangement.

This immediately struck me as odd as I wasn't aware of any form of compensation to the PM for any maintenance related activities, just 8% of gross rent and 1-month of rent to lease the property, per our contract.Naturally I wanted to understand the nature of this arrangement, specifically how much mark-up is being charged, so I referenced a specific sewer repair bill from 2015 that was $2,600 and asked him if he could provide the vendor invoice so I could understand how much the vendor charged and how much revenue the PM recognized.  

If you HAD to sell the glamping arrangement for some reason, the list of potential buyers would be smaller and likely only to attract investors. 

Over asking with a low rate might.From my perspective I would want to keep this a debt arrangement, not an equity one.