House hacking is a great way to reduce living costs while building equity, and BiggerPockets is a great place to network and gain insights.Good luck!

Short term rentals do get more money, but also cost more to run and require more time.  

-Transfer the property into an LLC – This may allow me to take ownership while potentially avoiding property tax reassessment, however this sounds like an involved process-Establish a living trust for my aunt and mother – The trust would specify that I inherit the property upon their passing and provide step up in cost basis but i'm worried that the living trust can be modified to have me removed (who knows what can happen) - My mother is somewhat volatile.I would like to live in the property and my mother will live in her second property with her husband. 

The marketing functions is where the very host cost comes in.

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

Underestimating rehab costs - get a contractor bid.5.

While the borrowing costs are higher, I’m exploring strategies where the returns could offset this.

As long as your purchase, rehab and closing costs fall below 70% ARV then you won't have to bring any cash to close. 

How much do you expect the rehab to cost?

I know the tax hit isn’t ideal, but I’m wondering if the long-term cash flow benefits outweigh the opportunity cost.