I'm considering a couple units. One is this one ($330):
It is 32A, IP66, 26' cord, but not a smart device. The one I linked uses the 14-50 plug I need too.
The other major one I'm looking at is ($650):
That one is 40A, NEMA Type 4 (this is IP66 equivalent), 25' cord, and is a smart device that allows me to schedule charging with the app or even using an Alexa device. But it does cost $300 extra, which is exactly where I established the "forget it" line. The fact that it is 40A rather than 32A maybe brings things into the sub-$300 difference range, plus right now there is a $50 off coupon on the page, so it looks like it's actually $600 right now. Add in the fact that it qualifies for a federal rebate... I'm thinking I might pull the trigger on this one.
Edit: I talked myself into the Wall Box while writing this. I just ordered it.
I looked at those options along with charge point flex, ended up with
Pulsar Plus Level 2 Electric Vehicle Smart Charger - 40 Amp NEMA Ultra Compact, WiFi, Bluetooth, Alexa and Google Home - 25 Foot Cable - UL Certified - Indoor/Outdoor - by Wallbox https://www.amazon.com/dp/B08H2LYFHX/ref=cm_sw_r_apan_i_JFFZWRX7S3MCT448T006?_encoding=UTF8&psc=1