Princess HM tends to sell faster than Wine and Dine. Essentially for both race weekends, if you're ready at the time of registration to register, then you will be able to get a HM solo event bib or a Challenge bib. The only time that wouldn't have been true is Princess 2021, but that was presumed to have a reduced availability.
Princess Weekend
2023
Challenge sold out in 65 min (
link)
HM sold out in 185 min (
link)
2022
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.
2021 (Presumed reduced availability)
Challenge sold out in 23 min (
link)
Half sold out in 26 min (
link)
2020
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
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)
2018
Challenge on "hold" in 16 min (
link) sold out in 67 min (
link)
HM sold out in 2 weeks (
link)
2017
Challenge on "hold" in 13 min (
link) reopened at 21 min (
link) sold out in ? (greater than 1.5 weeks (
link) and less than 6 months (
link))
HM sold out in ? (greater than 1.5 weeks (
link) and less than 6 months (
link))
2016
Challenge sold out in 105 min (
link)
HM sold out at approximately 7 hours (
link)