The importance of buying something that trades well cannot be emphasized enough. Sure, if you love to go to the same place every year, buying something that you love is always a good idea. We bought Maui for that reason. Buying something that trades requires a lot of thought. Never buy a trader in silver or even gold season. Always buy in platinum season.
My favorite purchases are Palm Desert, specifically Marriott's Shadow Ridge, lockoff, platinum season, reserving Pres week has been a great choice for us. January up to President's week is a bust, but live and learn. My other favorite is Willow Ridge, also Marriott, but it's Branson. Branson has a definite high season, which encompasses dates around July 4th.
We bought three Shadow Ridge and still own four Willow Ridge (selling two of those), and we have been very pleased with our trades, but so important to book ahead of owners that only own one week, because yoou can book at 13 months. We pay the lockoff fee of $95 and get two deposits into II. The trading power is incredible on those weeks. $164 Marriott-Marriott exchange fee. Works great, or at least it has historically worked great. Things change.