I'm curious what the claim process would be and what avenues the tenant might have to fight it.

No because it will depend on your tax bracket and whether you can claim rental income as QBI and whether you can even deduct losses from RE.

I was working with title companies to complete refinance paperwork for customers prior to this.

We still use the booking sites (AirBnB, HomeAway, etc), but we do most of our business directly with customers now through our referrals, networks, and website . 

You will need to claim that property as your "primary residence" for tax reasons because the bank will cross reference for that with an automated system. 

Last hearing I had was for damage deposit claim.

It's set to a loud volume because he claims he has sleep apnea (sleeping disorder) and can show a doctor's letter to prove it. 

Management company wants to keep pet fee, I want to claim the pet fee and be responsible for any damage.

And i was currently waiting to hear back from the city about just that...but i also found out from a lender that supposedly i cant get a construction loan for a multi family unit which is news to me...so i guess i have to look for a plan b which is single family home And the lenders reasoning behind that claim is? 

Proving your tip income should be no problem since you claim it all on your tax returns.. right??