I have preferences but not set on any market in particular.

The best will often ask for nothing until they set foot on the jobsite and really start with site set-up and demo. 

Does anyone have a set of questions or things they think through or scripts or anything that helps them approach, talk to, and close on deals with homeowners when they approach them directly (whether through mass marketing, driving for dollars, or otherwise)?

QBO isn’t made for REI out of the box, however, it is an amazing tool and really has amazing reporting when set up correctly.  

We do currently have around $50k set aside for our next downpayment as well (that’s in addition to a $25k emergency fund).

We are primarily looking for land on which to set up an owner-occupied situation with 1-4 rentals.

I made some of the biggest changes of my life but I'm setting my career up for long term growth. 

Scott Trench's "Set for Life" is for younger investors.

Instead, I've heard of hosts raising the nightly rate high enough it won't book or setting a 30-day minimum stay and had no issues with a double booking.

Your cabin will be set apart by the above, not by things you can get at Lowe's or Walmart.