It is cash you wouldn't have been able to finance anyway and easier to enforce than a judgement or bank levy. 

I would also bet that the late fee is wrong there as well as we now have the most asinine rule in the state for late fees.The laws are changing increasingly fast so I worry about the ability of BiggerPockets to keep up with all the legislative changes that are going into affect and how it affects the lease!

They become subrogated (steps into their insured's shoes with the ability to enforce their rights). 

*Chiming in on insurance - I have a few great brokers I can refer, my personal properties have gone down around 40% YoY.  2022/23 was terrible but there is new (insurance friendly) legislation that has encouraged more companies to come in.

I think we need to keep blaming the landlords and introduce additional rent control legislation to fix the issue. 

Would a cease and desist letter be the first warning for an STR if the city actually tried enforcing it?

The agreement you have with him may not be enforceable unless you or he have filed a Notice of Interest on the public record.

However, before adding the address to the system, they checked with USPS to verify, and came back denying my request saying the same explanation as what USPS said above.No one at USPS or the City has been able to provide me with any ordinances, laws, USPS Handbook rules, etc. as their basis for enforcing this decision.

A lot of them do grandfather old rentals but I have seen HOAs enforce the only 1 rental per community guideline for already rented properties and new investors!

TheOregon Department of Land Conservation and Development(DLCD) is issuing this guidance and model code language to helplocal governments comply with the legislation.