A trust offers no protection only anonymity.LLC can be pierced be a good attorney and you could trigger the due on sale clause where you would have to pay off the whole mortgage after transferring into an LLC.

Agree with all posted by Stuart & Corby, except about the Renters Insurance.We offer Renters Insurance to our tenants also and it's a special program only PMCs have access to and is a much better & cheaper "product" than tenants can get on their own.You have 3 options:1) Check the lease for a "transfer of management" clause to see if that can terminate those services.2) Negotiate with the tenant to terminate those services.3) Retain the PMC through the end of the lease.

Also, confirm local STR regulations are stable and transferable.

1) lying or intended to completely debunks any notion you have toward this argument.i should not have to go further but will2) if 20% off  coupons are the reason you expose yourself to liability with contractors doing your work(will make that point 4) or the deal is worth doing you're missing the forest for the trees.3) agents or buyers look at what date it was bought or transferred versus when it's selling. if it's short, it's likely a flip and buyer beware. the llc vs individual name doesn't mean much to the credence of the grade; buyer speaking from first POV.to add...4) liability is why you do it, you're fully exposed. grabbing pennies, costing dollars.

Pitfalls—What should we watch out for (transfer taxes, reassessments, lender issues)?

Learn the system that all people, accountants, CPAs and all are going to use which is quickbooks so you know it and it can be transferred easy when you are ready to move from self managing to bookkeeper to accountant. 

Free transfers are nice, but clean records and automation are priceless! 

Make sure it spells out the percentage interests, the exclusive-use/occupancy plan, a clear maintenance matrix (who pays for interiors versus roofs, foundation, major systems), reserves, right-of-first-refusal so transfers don’t get messy, and dispute resolution that doesn’t require World War III to enforce.

Once ownership is transferred via foreclosure the owner can file for eviction against any occupants including the previous owner. 

I feel like if I profit 50k, I would be fine to just transfer that money and get back the money I put into improving the property.