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You can disregard my post to your other thread.
What you suggest is certainly doable at least for scenario #1. However, with Marriott, you don't have to prepay your annual maintenance fees. You can place requests before you pay them. The annual fees are due around Jan 15th of each year -- you will receive a bill sometime in December.
As to the difficulty of the trades you suggest:
#1:
I'm not an expert on what are the most popular weeks at Desert Springs/Shadow Ridge--the II book shows Christmas(week 51) in that region as slightly less popular then the Feb/March time frame. Still you should secure your week as soon as possible -- as you suggest. The other half of the equation: Aruba, II shows week 52 as significantly more 'in demand' than Christmas week(week 51). So while not an easy trade, if II's demand chart is accurate (some would question its accuracy), it should be easier than trying to get week #52.
#2:
With II you can't request a 2BR unit with a 1BR unit (outside of flextime--60 days before your requested week). Hawaii is a tough trade using like for like (2BR for a 2BR). Trying to get a 2BR unit with a 1BR is questionable. Trying to get this type of trade in flextime is possible but I wouldn't count on it. Also, doing this in a 60 day time frame with trying to coordinate airfare, especially now with the current airline situation could be very expensive. One alternative is to book a hotel res. so that if the trade doesn't come through you have a back up and can go ahead and book airfare without having to wait for the exchange to go through.
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