I'd like to thank the guys above for resurrecting this old thread since I'm a newb needing a 15th post.
It's interesting because just when the OP started this I was buying my 2019 TRD OR. I was planning to play the "wait" game too, but the truck I fell into was "exactly" what I was looking for right down to the color and low mileage so I pulled the trigger. I'm not unhappy with it because I'm now a year into it instead of still looking. And, prices have not improved all that much.
Also interesting to read the different takes on what is important to folks in their individual decision making process.
OP, what did end you up doing?