Welllp 4 days later, and I'd say it was a success.
Kid never cries more than 10 minutes to fall asleep or when he wakes up in the middle of the night. Average daily sleep went from like 13-14 hrs to 15-16 hrs. Kid is just overall better well-rested and happy when he's awake. I'm sure there will be steps back at some point, but dang I can't believe how well that worked.
My wife and I have had 3 nights straight of 8+ hour sleep, uninterrupted, which hasn't happened since he was born. Wish we had done cry it out about 3 weeks sooner!