When I approach them for financing on my next property, I want to avoid raising any red flags due to my relocation and the status of my Tennessee home via how I file taxes in 2024 (i.e STR instead of my primary as it was originally intended).  

Quote from @Brendan Jones: When it's a home you intend to live in, I lean towards focusing on what you want, then making it work as best you can as a short-term rental.

So your answer depends on lien priority, and you are advised to learn which liens rank higher and lower in priority (and why); that is beyond what I intended  to post here.The prothonotary should have some way to indicate a lien’s status - whether it is open or satisfied or discharged.

You may be able to refinance with rehab on the property you intend to sell.

.- Due to my position on the board for the condo association, I am aware of long-term large projects that the association intends to embark on.

Interviewing multiple GC's is the best way to operate, but make sure you are communicating to them that you may want to limit their scope of work as you may intend to SUB out some of the work ourself. 

MLS photos are intended to make the property look as good as possible, that's why actually going there is key in pulling accurate comps.

Tell us what you really think of the opportunity and ask more specific questions.

I jumped at this opportunity buy getting my license, signing up with her broker, only to discover all she wanted was the sign on bonus from me joining that office.

If you intended to flip but now want to hold, that's one of the major reasons DSCR loans exist.