I am assuming you are talking about the HHonors rewards. I was a Diamond VIP for a small time and I have to say; no it is not automatic. First, there has to be an upgradable room, normally at Hilton named hotels that have towers/executive levels. (A one bedroom to two bedroom suite is not consider an upgrade. Upgrade is more like bottom floor no view to higher floor with a view. This is really geared towards business travelers) You have to ask when checking in if there is a upgradable room available. (It must be available for the whole stay not just part) Lastly, I have done upgrades as a Gold rewards member, so it really does not make any sense to try to achieve Diamond status. If it happens, it happens. The only worth while benefit at the Gold and Diamond level is the complimentary breakfast, and some places mid-afternoon snack. The best benefit, regardless of level, is the mangers reception where the first couple of alcoholic drinks are free.
Remember this is for hotel stays and not timeshare stays. The HHonors VIP levels does nothing at the timeshare resorts. For example, if you where staying at the Lagoon Tower at HHV, you will not get a free voucher for breakfast for being a Diamond VIP. However, if you convert your HGVC points to stay in the Hilton Hotel, then you are eligible for the free breakfast, up to two people.
Also, let me be the first to say, it is really not worth buying HGVC timeshare retail to become a Diamond VIP member. In the long run you will save much more money buying resale, and forgoing the HHonors reward status.
This is the new HHonors policy from their website:
*Executive Lounge Access Policy
If you select a space-available room upgrade as your on-property VIP benefit, the following policy will apply effective August 15, 2008, at all Hilton®, Conrad® Hotels & Resorts and Doubletree® hotels:
If you are a Gold VIP, you'll be given access to the Executive Floor lounge when you receive a room upgrade to the Executive Floor. If an Executive Floor room upgrade is unavailable, you'll still receive daily complimentary Continental breakfast in lieu of lounge access.
If you are a Diamond VIP, you'll enjoy access to the Executive Floor lounge, even if you don't receive a room upgrade to the Executive Floor, including daily complimentary Continental breakfast.
At hotels without Executive Floor lounges, Gold and Diamond VIPs will receive complimentary Continental breakfast for themselves and up to one additional registered hotel guest each day. If breakfast is included in the room rate, you'll receive an alternate welcome amenity that varies by hotel.
I have been at Diamond Status for the past three years with HHonors. I am at the elite plus level not the elite premier level with HGVC. My Diamond status was achieved because my business required to travel and I stayed at Hilton properties. I have had upgrades on numerous occasions and the diamond status gives you access to the executive floor lounges if one is available. The room upgrade is is pending availability. I have also been upgraded when I was at Gold status. I expect to revert to Gold status next year because my business travels took me other hotel chains. I think the main advantage to Diamond Status is that you get a 50% bonus on HHonors points for your stay. This means that HHonors points accumulate much faster. You get a 25% bonus with Gold Status.
Going Global is a great option that HHonors provides. This can give you six free nights in a category 6 resort for 175,000 points or six free nights in a category 5 resort for 150,000 points. We have used HHonors to have vacations in San Diego California, San Juan Puerto Rico, Budapest Hungary, Amsterdam Holand, Los Cabos Mexico, South Lake Tahoe California, Scottsdale Arizona, and Chicago, Illinois. We will be cruising with HGVC next year and our hotel rooms in Barcelona will be covered by HHonors. I have never converted HGVC points to HHonors point as of this point in time.
I would not advise purchasing 34,000 HGVC points just to have Diamond Status for life. You get Gold Status for life with 14,000 HGVC points. However, HHonors is an excellent program and I urge you to learn more about it and enjoy the options that it provides.