We can put more than one on the waitlist, right? If so, in order of preference?
You can have multiple requests. There are two scenarios for getting a request filled: an owner does nothing with their owned week and it automatically passes from HRPP to CUP or an owner turns in their owned week prior to the HRPP expiration date for another week or resort.
If an owner of a week 51 (I'm using week 51 since that sounds like the week you want to book) does not elect to use their owned week 6 months prior to week 51, the week will automatically pass from HRPP to CUP and becomes available for use by other club members. In this scenario, I believe you could create a preference for multiple requests with Hyatt as all the weeks would become available at exactly the same 6 month window. I say "I believe" as I've never done this - but it seems that Hyatt has to have some selection criteria in place to address which week you are assigned. This is definitely something that you'll have to call the Go Hyatt staff on. I'd be interested to hear what they say.
If a week 51 owner turns in their HRPP week PRIOR to the 6 month HRPP expiration date, your preference priortization goes out the window since which ever request becomes available first is the request that will automatically get filled. IE: if your order is Park Hyatt, Mountain Lodge, Grand Aspen then Main Street and a Main Street week is turned in 6 months and 1 day before your requested check in date, you will automatically get Main Street. Since your request was filled prior to the Park Hyatt, Mountain Lodge, Grand Aspen weeks passing from HRPP to CUP, you will not have a chance for any of these weeks.