I want to know if there's a good chance that a buy and hold investor would let me know if it's a potential deal.

@Kyle Johnson is there a potential insurance claim for the roof?

I have a ton of potential clients too for you.

If the contract included clauses about assignment and the ensuring processes like realtor showings and potential sale to an investor, and you signed this agreement, then legally, the company can proceed as outlines, even if the reality doesn't match your initial expectations. 

But my understanding is also that there can be tremendous tax benefits / write offs when it comes to real-estate.I am looking for more guidance from professionals on how to structure my investments and how I could potentially harness the power of depreciation and write-offs to legally save money on my active earned income.

For individuals navigating the demands of a w2 job and grappling with substantial tax obligations, exploring the potential of short-term rentals unveils a compelling avenue to mitigate tax burdens.

You will most likely have to pay HOA penalty fees, fees by the state if they have tenant rights in place and potential lawsuits from the tenants.

To maximize the potential I would consider moving every year if that's possible. 

But also something with a CRM to store clients and potential clients for follow up.

Properties that are very easy to set on auto pilot collecting high rents with potential of easy to manage tenants.