I'm in the same place I was earlier this week before MW registration occurred. I suspected MW would be nuts, but even I probably undersold how nuts it actually ended up being. I don't share that same level of concern for Princess at the moment. I'll have my multiple devices and multiple browsers and feel relatively confident I'll likely be able to get my two 5ks and one challenge. Ultimately, you have to do what makes you the most comfortable with the level of risk in terms of not getting in.
Ignoring the registrations that we believe had reduced capacity, W&D 2022 sold out faster than 2017, 2019, and 2021. And MW 2023 sold out faster than 2017, 2018, 2019, 2020, and 2022. So both of these would suggest that Princess 2023 is probably more likely to sell faster than anything in the less several years.
Princess Weekend
2022
Start (
link)
No more queue after 21 min (
link)
10k sold out in 23 hours (
link)
5k sold out in 2 days (
link)
HM sold out in month (
link)
Challenge unknown sell out date
*5k, 10k, HM periodically open after sell out in 23 hrs.
Yoga sold out in 3.5 hrs (
link). Registration was about a month after normal registration.
2020
Start (
link)
5k and 10k sold out in 97 min (
link)
Challenge sold out in Sept 2019 when registration was June 2019 (
link)
HM sold out in Dec 2019 when registration was June 2019 (
link)
2019
Start (
link)
10k sold out in 57 min (
link)
5k sold out in 10 hours (
link) *Post about 1 hr earlier states only 10k sold out thus far
Challenge and HM still open 2 months later (October with August registration)
(link)
Challenge sold out sometime between 2-3 months based on this and prior post (
link)
In all three years of Princess data, if you were ready to register at open, then you got what you wanted. Not looking at current races for other weekends, Wine and Dine 2021 you would have cut it close even at open. MW 2022 and 2020 you might have had issues even at open as well.