Not quite correct. The Surpass card only gives you automatic Gold status the first year. I'm not sure what you have to do ($20k/yr?) to get it again the second year, but just holding the card is definitely not enough.

So for the long term, unless the spend to maintain Gold on the Surpass card is signficantly less than on the regular (no annual fee) HH Amex, I don't necessarily see the point in holding the Surpass card (past the first year) for the status (unless you're going to achieve the $40k/yr spend and value the Diamond status).

Regarding Gold vs Diamond at HH: Both give you free breakfast, free internet, and upgrades (when avialable) at all brands worldwide all days of the week. So if that's the main perks you care about, HH Gold may be quite enough. HH Diamond has some additional benefits, but they may not matter to many people enough to jump through hoops to get Diamond rather than just Gold.

I have both HH Amex and SPG Amex.

Raw rewards are better with SPG Amex....that is, I tend to get more out of 1 SPG than 3 HH. But I use the HH Amex for a few months every other year to lock in a good elite tier there so I have a backup option when I'm traveling somewhere with better Hilton options than Marriott or Starwood.

The problem is that HH points are pretty useless on the short weekend stays. The OP would be holding the points for the 6-night European or Caribbean stay. That might not be a bad strategy...although I'd check the HH board here and make sure your target properties aren't ones that game the system and make a "standard room" award impossible to get.

You could also get the SPG Amex and have enough signup bonus points to fund a few weekend getaway Cash & Points awards. The strategy there might be to always compare your likely Priceline option vs. the SPG C&P option vs. (maybe) your Priority Club option. But you'd make HH Amex your primary spend card and know that the bulk of those points are being saved for the European trip.

Annual spend levels obviously play a role. If you're a $40k/yr guy, you're looking at probably 18-24 months before you're booking your first fairly high-end award week on CC points alone. SPG Amex is more of an instant gratification thing: every couple months, you could be doing a weekend C&P award using the points you earned on CC spend the prior month.

If you can use a property with points+money rates (which are often the best value, but not always avialable), I find HH points not at all useless for shorter stays. In fact, the only 6-night stay I've ever done (which I haven't started yet, but will soon, and already booked) is a points+money stay, that would be exactly the same amount per night whether I did 1 night or those 6 nights. (And I booked during the time around the turn of the year when they had the promo for 30% back on points+money bookings made then for stays this spring. So that means I will use even less points in the long run.)

I realize that some properties have special rates for long stays, but they don't necessarily beat the value of points+money awards (which, in turn, eliminate the worry about how long your stay is affecting the points needed per night).

Oh, man, I had not realized this. I was thinking of getting this card for the Gold status, but you are correct, it's only for the first year. Just as with the regular HHonors Amex, you have to spend $20K to get Gold beyond the first year; otherwise just Silver. AFAICT the Surpass card offers little incentive to keep it beyond the first year unless you spend an awful lot on gas and groceries (and, uh, Hilton stays) such that you could hit the $20k spend almost entirely in the bonus categories.

My problem is that I've never actually seen a points+money award available anywhere I'd like to stay.

Agree with you though...similar concept to SPG, if you can find one, that can be a good way to get meaningful value from a program if you have a smaller throughput of points (e.g., just from a credit card). I have pretty good luck finding my desired SPG C&P awards, although it isn't always at that city's top Starwood. (e.g., The best W or St. Regis won't have it, but the midrange Westins will.)

I hope this is an area of HH that gets stronger over time. Or at least stronger in relation to other parts of the program (is that too cynical?). Having greater ability to use HH points on a short stay without feeling like I'm taking a huge value hit vs. AXON/GLONP2 type awards would make the whole program more valuable.

The hotels at which I've used Points+Money were Hilton Buenos Aires last Dec and Hilton Madrid Airport coming up next week, in each case booked several months in advance. I'm not sure if it's the hotel or the far-ahead-booking (or both combined?) which made the difference.

My last 4 stays were 1-2 days. At 3 of the 4 I got redemptions below the "normal rate for that day. All were roughly 5-6000 points below the normal rate for that hotel. This happened at Hilton London Metropole, Hilton Chicago, Hilton Antwerp. Maybe I'm lucky, but I have been pleasantly surprised. At this rate I won't miss the elimination of Point Savers at all.