The point of my 8-stay experiment was for me to decide whether I think Diamond is worth it for me. As always YMMV
For a few days after I returned my HH account was only showing 7 stays, with one of the Doubletree stays showing up but with no points or stay recorded against it. I rang up the HH enquiries number. If there is some special Diamond phone number I could not find it. I spoke to someone in some far off foreign land who informed me that because I had stayed in the same Doubletree on 2 separate nights close together it would only be recorded as one stay. I had to point out that the 2 Doubletrees I stayed at were separate properties in separate suburbs of Aberdeen. He then said I would have to ‘email my folio’ to the HH email address (which he didn’t volunteer). This was frustrating. But luckily when I checked my HH account again the next day, 8 stays were showing and a total of 41,000 HH points, which amazingly is enough to stay at the Doubletree in Melbourne if I choose to stay there on my upcoming trip. My IHG points always seem to come up about 100 points short of whatever IHG hotel it is that I’m considering staying at, so to have enough points for a free night was a refreshing change
Did Hilton honour its alleged Diamond benefits? (I’m sure you see what I did there
).
Free breakfast – 7 out of 8 hotels said I could have free buffet breakfast in the restaurant. The other one said I had chosen a different option on my profile, which I think is incorrect but didn’t care at that particular hotel. 1 hotel had additional breakfast choices available at a charge, as well as the buffet. All of the hotels had hot and cold buffet choices, and I wasn’t limited to continental breakfast only or anything like that. Luckily for me I don’t drink coffee so I didn’t have the issue that seems to plague many HH members of being asked to pay for decent coffee at breakfast.
Unlimited milestone bonus – I don’t actually understand what this benefit is so I have no idea whether it was honoured (or HHonored).
Lounge access – 2 out of the 8 hotels had lounges, which isn’t a very good percentage. Neither of those lounges would entice me to choose those hotels again. Last December I stayed at the Conrad in Singapore and paid the room rate that included lounge access, and the Conrad lounge was way better than the ones in Edinburgh and the Hilton Park Lane in London. But when I go back to Singapore in July, I’m thinking of staying elsewhere because I feel like I’m ‘over’ the lounge at the Conrad and I want to try somewhere else. So I guess lounges aren’t a huge drawcard for me, even good lounges.
48 hour room guarantee – I didn’t need that benefit.
Status extension – I don’t understand what that benefit is either.
Elite status gifting – I suppose that means that if I stay enough nights I can give some status to someone else. As my account is currently telling me I need another 50 nights at Hiltons to renew Diamond next year, I doubt that status gifting is going to be a benefit relevant to me
Upgrade, up to 1 bedroom suite category – I generally find it really hard to know whether I’ve been upgraded, firstly because I can never remember what room category I booked and secondly because unless my room is a really obvious suite I can’t tell. An extra square metre of space might count as a higher room category to a hotel chain but to me it’s fairly irrelevant. I feel like I got noticeable room upgrades at both Doubletrees, the Curio Trafalgar St James and maybe the high floor I got at the Hilton Park Lane. Otherwise I couldn’t tell you whether what I got was better than what I booked. Also, I’ve stayed at many hotels without any status at all and I’ve quite often been told at check in that I’ve been upgraded. Being upgraded is hardly an exclusive preserve of being Diamond or even of having status.
2 bottles of water – no water was provided in Edinburgh, although there was a lounge so maybe that was instead of water but the Hilton website does seem to imply that water and lounge access are separate benefits.
Late checkout – I didn’t need this benefit on this trip. I’m sceptical about how easy it is to get late checkout anyway, because I’ve often heard about people being told the hotel is fully booked and late checkout is not available. I sometimes ask to pay for late checkout and even then I am sometimes told it’s not available.
Premium wifi – I did not notice any difference between the wifi on this trip and the normal wifi that you get as HH blue or silver.
Overall as a Diamond I did not feel like I got anything that I could not have purchased if I really wanted it. There wasn’t any indefinable quality to Diamond status that was not also available for cash. A high room category, lounge access and breakfast are all freely available to those who pay for them. At least half the time my room was not ready when I arrived, and it would have felt like a genuine Diamond benefit to me if Hilton had arranged my room to be ready on arrival and I didn’t just get told like everyone else ‘check in is at 3pm’. I still prefer to have breakfast in peace in my room rather than have to get presentable to go to the restaurant or lounge for breakfast, even if it is free.
Seeing I do not stay 50 nights per year in hotels, it would be more cost effective for me to pay for a fancy room or lounge access on the one or two occasions a year that it would matter to me to have those things, rather than to chase Diamond status. So all in all, Diamond was nice, but I’m not going to bother to go out of my way to retain it. On the whole I think I was more impressed when I had Accor platinum, because that regularly meant I would find deluxe chocolates in my room
And PS, north east Scotland is beautiful
After arguing with staff, and the receptionist Manager being summoned (still not able to find my status in computer), they gave me 50% off breakfast. Best they could do! 
