But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

You have provided a variety of situations where doing a cost segregation study would be useful.  

This was the kind of situation where most people would turn around and walk away, but not us.

The episodes I struggle on there are the interviews that seem to be either someone the host wants on, or that they were on their show and it’s a reciprocal situation to build an audience.

Multiple offers situations are the rare exception, not the norm.

I’m unfortunately in the same situation.

Definitely not willing to put money into something like this and potentially worsen our situation.  

How would the situation differ with a home that’s never been a STR but would become one, or a home that’s for sale now that is a current STR.

I am in the same situation.  

Your ultimate goal is to create a “Win-Win” Situation, for you and the seller.