Thank you! Have never heard of Surpass.
Glad to let you know. I've been a happy user of Surpass (and it's Citi predecessor) since 2008. I tend to like the Hilton Honors program as it's pretty easy to use. Properties cost varies a lot, but in places like Allentown a Hampton is ~35,000 pts, in NYC Times Square the Doubletree is like 95,000pts and I'd say most are generally 70,000pts so that can help you compare to other systems. These are all standard room rewards, there are upgrades for suites, but those are "insane" pts costs to me. The 5th night of a points stay is free, so that's cool.
But for me, the best part is the free night reward - It's just that. There are no blackout dates, you can use it at a Hampton or a Hilton or pretty much any property. I recall comparing other systems, and their reward nights were more limited - certain tiers of properties, or you got a "free night" each year that was actually a number of points, which again limited where you could use it. I know the HHonors reward stay is no joke, my sister also has this and used one to stay at a Hilton property in Times Square on new year's eve. It was $2,500 for the night cash, but a free reward for her.
On the cash side - Hilton's aren't the cheapest, but they do have competitive rates IMO. More than that however, they tend to have something where you're going. It's very rare that there is NO Hilton property, even "out in the boonies" which greatly complements timeshares.
The downsides I think is mainly the progressing loss of even mini-fridges in the rooms, and they certainly cost more than timeshares if you want or need 2 BR. However, I also think this might be most hotels.
