Hello, 4 yrs old owner from resale market just like you. the general rules of thumb is if the locations with more than one HGVC property normally easy to book. (NYC, Orlando, Vegas, Hawaii, Myrtle Beach, etc,,,) I can find a one bed room or studio about 1 or two months out easily peak or non peak season. Mexico is great, this is one of the main reason we go with Hilton over Marriott, since Marriott has no Mexico properties. You can always find opening through out Mexico two to three months out.
Place to Rule out you asked?
1. FLORIDA outside of Miami and Orlando, impossible to get in. most of those properties are old and the original owners are refuse to convert their fixed weeks to points. I have NOT seen any three days opening in my entire 4 years with HGVC.
2. Hilton Heads, this is a number two impossible to get in, I do see opening everynow and then months ahead, it's doable, but very difficult.
3. Ski Resort, if you want to book two to four bedroom between Jan to Mar, you can forget about it. One bedroom or studio,,,, there is a chance. A slim chance. You will find more availability in April, but the ski season is pretty much over by then.
Outside of these three, I think HGVC is great. BTW, I paid 5k for 11,500 pts with 1500 HOA annually. let me know if you can beat that at the current market.
Happy Travel,