Sooooo, after today and really thinking things through about the trade-in process, I'm just not pleased with Tesla taking their time and giving lowball trade offers.
Carvana offer was $2,000 more than Tesla, and out of curiosity I tried CarMax which came in another $2800 HIGHER than Carvana! I have an appointment with CarMax and hope to come out nearly $5K higher than Tesla's initial offer for my car. Let me be clear, my trade is in the $20K range, so a few thousand represents a pretty big percentage.
I'll have to figure out logistics when my MYP is ready but I think for $5,000 extra in my pocket it's too hard to turn down. It does seem like Tesla is actually discouraging trading in at this point.