It went ~okay~ - the TYM / LS dealer was closed and it almost looked abandoned, so probably not an option.
I ended up testing positive for covid on Saturday, so I cancelled the visit to the tractor until I'm better. Prior to feeling poorly and realizing I was sick, I did go to see JD / Kubota with my dad. If we're going with how I felt about the dealer, I preferred the JD - they were really helpful, and even showed me used 1023e (with loader and upgraded seat) that is a couple years old and has 88 hours ($12K). They were pragmatic about what I needed and was comfortable with / had space for, and didn't pressure me into making a decision.
The Kubota was an more intense sales pitch versus just trying to figure out what I was comfortable with / needing for my property. Thanks to you guys, my eyebrow raised when he dismissed the B series I was looking at and walked me over to a enormous L series to assert I'd regret not spending $40K on the equipment I needed.
That's how it went - I have already purchased a mower from the JD dealer and I've had a good experience with them, getting my mower serviced annually, getting parts / customer support on my other equipment issues when I mess something up, etc. I have some thinking to do when I'm on the up and up.
Thanks for the continued discussion, everyone! I have learned so much!