I am at the Elite Plus level. I purchased all 24,000 points directly from Hilton. I have only recently joined TUG and learned about the resale market. I visited EBAY for the first time several weeks ago. All that being said, I have had a great experience time sharing and cruising with Hilton and basically got what I paid for, although I could have had roughly the same for less money. I am very happy with my purchases and have no regrets. My philosophy is to enjoy my current points and perks.
The main advantage of Elite status is that you are automatically HHonors Gold for life. This means that you get 25% additional HHonors points if you stay at a Hilton Hotel and an automatic room upgrade if one is available. If your work requires you to travel, this is a major perk. Is it worth the extra money? I doubt it. However, I have used HHonors redemptions for numerous vacations and the points do add up quickly. You can also bypass the 1 in four rule and book Grand Mayan and Club Intrawest directly through HGVC and bypass RCI completely. I did so with Grand Mayan Riviera Maya earlier this year and will be doing so again in the near future with Club Intrawest in Whistler, BC. This is a very nice perk. Is it worth extra money? Once again, I doubt it. The main advantage of Elite Plus status is that you have same year point conversions, instant RCI confirmation, and access to special RCI resorts on a quarterly basis. This would be very useful if you want to go skiing in Lake Tahoe or Vermont during peak season. Is this worth the extra money? Once again, I doubt it. However, when I add up all the increased flexibility I have as an Elite Plus member, I do not regret my purchases.
The main advantage of Elite premium is that you are HHonors platinum for life. This gives you a 50% bonus on all Hilton Hotel stays. This means your HHonors points accumulate very fast. You also get automatic room upgrades if available. However, I have been at the HHonors platinum level for the past three years due to my business travels without having Elite premium status. Unfortunately, I will most likely go back to HHonors gold sometime next year because I am being required to go to more Starwood and Marriott properties in the course of my work. However, I do pick up Starwood and Marriott points. (I have yet to have enought points for a good redemption with either Starwood or Marriott, but I am getting close.)
Starwood has a deal where if you purchased a previous property resale and then buy a new property from Starwood, you can retro the previous property so that the previous property will have StarOptions even if it is a non-mandatory property. I don't know if Hilton has such a policy because in Hilton, points are points. Hilton has treated the points of resale owners the same way they treat the points of people who purchase directly from Hilton. Frankly, I think Hilton is a shining light in the time share industry.
By the way, without people like me who purchased directly from Hilton, the resale market would not exist. Good luck whatever you decide to do.
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