If you are uncomfortable negotiating, hire a realtor to do the negotiating for you.  

If you're uncomfortable with the answers you are getting, make the sale contingent upon vacant units.

It's easier to hold yourself accountable when there's a routine.

The higher price point, makes me feel uncomfortable with the risk of it a STR potentially not doing well at that price point for the area, but I'm also eager to get started and have enough capital to get started.

My advice:Get a business plan of where you want to be and work backwards to layout the steps needed to get there.Get your systems and tech in place now, so its routine and you can scale with ease. 

But that just looks like somebody that tried to continue with the inflated price routine as things shifted.

After realising I would like to make some more money, better my life, and live more comfortably in a very uncomfortable state, I am looking at multi-family properties. 

That may sound like a decent return, but I am paying ~ $100/month for trash and water, $560 on tax/PMI/insurance/principal/interest, plus about another $100/month on routine maintenance and upgrades. 

My life is a little chaotic and unpredictable these days but despite that, it's helped me establish consistency, a healthy routine, and everything is on track with the investment goal :) Really recommend it!

If you are uncomfortable, which you probably should be, then write a cancellation letter and ask for any deposit back now.