I am currently 21 years old and was recently hired with my dream job in Sarasota County (I saw that Sarasota wasn’t an option so I picked the closest.)

These solutions can make a huge difference, and the long-term option will really help set your STR up for success.

I'd see how next 2 weeks go before lowering the price.

There are significant advantages to investing here (lower barrier to entry, much better price to rent ratio's, etc. etc.).

We take your info and we let Lenders battle for the deal offering their best options.

Alot of unknowns as you don't have the ability to walk the property beforehand, but interesting process, and pretty good deals exist there.While the Trustee Sales are cash purchases, there are many hard money options that can turn over the funds in time for the 24 hour funding required to complete the purchase.If you are interested, let me know and I can go into more detail, as well as make some other suggestions for you to consider. 

Mean while i would be building equity, and if rates do lower, or when the term ends, could refi for better rates and then maybe cash flow.My questions are:Is this too naively optimistic?

My question again stems around using seller financing to allow them to receive a consistent monthly pay of X amount and delay/lower their tax bill in the short term instead of going through a lender to borrow 800k+ causing my mortgage to be significant part of our income roughly 40-50% of take home -  which we are approved for LOL.

Your mentor’s advice about starting with a rental property is solid, and a duplex could be a great option for house hacking.

Now, the older, house-hacked duplex comes on the market as a rental, lowering rental prices as another option available.Someone else moves out of their rent by the room unit, and upgrades to the duplex.