He kept avoiding our requests and said we should claim it in our 2023 taxes instead… The last straw for us was when he tried to charge us another $7.5k to file our taxes which obviously ended our relationship instantly.

And the owner is paying you not only to enforce common sense rules, but to understand the ADA and the proper & legal way to hande a request for a reasonable accommodation.Most city and county governments have a position called an ADA Liaison (or something to that effect) whose position exists to train local businesses and landlords on ADA requests and what is reasonable / unreasonable as it pertains to accommodations (often the same person that gives training once or twice a year at the local Board of Realtors, so you might even be able to reach out to them for a point of contact).Rather than operating in a vacuum, or taking your advice from a public forum, why not reach out to that person in your jurisdiction and get an opinion straight from the horse's mouth?

You should advise the roommate that they are welcome to submit a request for accommodation but unless they have a plan that would alleviate your symptoms their request will likely be denied.

Hello  , One of our tenants just requested to fill in landlord paperwork for the Rental assistance program.

I just sent you a colleague request with a bunch of questions. .. ha

She is requesting I reimburse her for the $150 she spent on these very specific particular wall anchors, if she needs to replace them.

A landlord does not need to provide a reasonable accommodation for an emotional support animal when:The property is an owner-occupied building with four or fewer unitsThe property is a single-family home sold or rented by the owner without the use of an agentThe emotional support animal poses a risk to the health or safety of other people, or a risk of substantial damage to property (but this risk must be specific to the animal and cannot be based solely on assumptions about the animal’s breed)"Definitely have a chat with a local attorney to ensure your local laws apply, nonetheless since its an owner occupant, it sounds like you have some recourse to deny this request. 

Unless I'm reading it wrong its just a loopnet listing. you're right i can't find the 7 million closing request.

They deliver an envelope that has a notice we own the property, instructions on how to pay rent, how to request repairs and two lease offers. 

In Maryland there is a law if it is not recorded the borrower at any point can request all payments be reimbursed back to them.