To my knowledge, there is nothing definitive about the quirks of runDisney registration queue acceptance. Your best bet is multiple devices, multiple browsers, and opening some before the link is to go live and some after the link is to go live. Spread out your options and see which one is the winner. I've been around for years worth of registrations and have yet to see one definitive method that beats other methods.
Here is some information that may or may not make your decisions easier. Wine and Dine Historical Sell out timing:
2020 Race (Reduced availability?? or Villain theme??)
Start (
link)
5k and 10k sold out in 46 min (
link)
Challenge sold out in 86 min (
link)
Half Marathon sold out in 126 min (
link)
*2020 registration was March 10th, 2020 which was before most of the world pivoted due to COVID-19. So it's hard to say this race actually did have reduced capacity. It is more likely that this race sold out quickly due to an anniversary year in combination with the newly announced Villains theme. 2021 will also be Villain themed.
2019 Race
Start (
link)
10k sold out in 84 min (
link)
5k sold out in 8.5 hrs (
link)
HM sold out in three days (
link)
Challenge sold out in May when registration was in March (
link)
*There were brief occasions when these races opened back up again for a few moments.
**Couldn't find the 2018 Wine and Dine thread
2017 Race
Start (
link)
10k sold out in 3 weeks (
link)
HM sold out in 4 weeks (
link)
5k sold out in 5 weeks (
link)
*No mention of when Challenge sold out
Based on this information, the HM sold out in 126 min, three days, and 4 weeks in the three years surveyed. The 5k sold out in 46 min, 8.5 hrs, and 5 weeks in the three years surveyed. It would appear in either case that as long as you're ready to go once registration begins, then you should be fine with both the 5k and the HM. However, the 5k is more likely to sell out faster than the HM based on these three years of surveyed data. With that being said, we don't know how 2021 registration will play out in the first post-COIVD registration period.
If it were me, I would register for the HM now, and then I would attempt to register for the 5k during general registration. My reasoning is that you have no interest in running the 5k alone. So in either choice you're registering your son in general registration. So to me, it's an "either I get it for both of us OR I get it for neither of us" situation. You are likely to gain mere seconds in difference of time when comparing the process between a single 5k registration and two 5k registrations. While seconds could matter, sell out history above says you're more likely operating on the scale of minutes to hours at best. But that's simply my opinion and insight.
Just be sure not to waste time on things that can be edited post-registration confirmation. Like estimated pace, t-shirt sizes, etc. Just choose something and move on. Edit it later. I feel like Name, address, and email are probably the most critical and those should be easily accessible (maybe even autofill) from your runDisney account.
Hope that helps!
