Wine and Dine Half Marathon Registration

If I want to register for the challenge for me and my husband, but only want to add the 5K for me, will I be able to add all that at one time, or will I have to grab the challenge first and then go back and try to register for the 5K? I'm experienced at registering both me and DH, but the add on of the 5K is what I'm confused about.
Each event would be a separate registration step, meaning you would add challenge you, challenge, husband, 5k you. (And hope one or more don't sell out before you get to pay)
 
If I want to register for the challenge for me and my husband, but only want to add the 5K for me, will I be able to add all that at one time, or will I have to grab the challenge first and then go back and try to register for the 5K? I'm experienced at registering both me and DH, but the add on of the 5K is what I'm confused about.
You have to complete each registration individually, but can do it all within one purchase. You would complete a registration as usual, and then at the bottom of the screen there is a button to "add another registration" (or some wording similar to that) and you just select that and complete the next registration. You can do all of this through either your rD account or your husband's, just make sure that you are using exactly the same information for whoever's account you are NOT in so you don't have the "disappearing registration." (For example, my husband's name is Matthew, but in his rD account it's set up as "Matt" so that's what I have to use when I register him.)

As stated above, there is a chance that one of the events could sell out before you complete all 3 registrations since your cart items are not "held."
 
How difficult will it be to sign my sister and I up for the Wine and Dine half marathon? I know that some weekends are more difficult than others and certain races within each weekend are more difficult than others. I would like to book our room with my DVC points as my home resort keeps flip-flopping from available to unavailable, but in order to do so I will need to borrow points from next year which means no putting them back if we don't get it. I could always just wait and make sure we get in before booking, but then I run the risk of missing out on the room. What to do, what to do!?
How can someone from INDIA want to join the Wine & Dine Marathon? I am excited and want to join.
 
How can someone from INDIA want to join the Wine & Dine Marathon? I am excited and want to join.
Registration for this year’s event is already full. It’s unclear when next year’s registration will take place but the pic below shows the registration dates for the current “season”, I’d guess next years will be around the same time. Be aware that if you want to sign up, you’ll want to be on the registration minutes before it officially opens up, the races have been selling out very quickly for the last couple of years.

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