Given the freebie method of accumulating Hilton HHonors points through cards, you should be able to do two sets of two apps about 90 days apart for the Citi Hilton cards. Also get an Amex Hilton card. Some will go for the Amex Surpass, some will go for the Citi Hilton Reserve card in order to get status. That will give you a stash of over 250K HHonors points.

Since status is not important to you (and by the way, with Hilton, most seem to agree that Gold is the sweet spot--free wifi and breakfast, extra point accumulation, sporadic upgrades compared with Diamond--and there are several much easier paths to Gold than spending $20K per year or holding the Reserve), the lowest level Hilton status, Silver (given simply for holding the Citi Hilton card), opens the door to GLON awards while holding the no-fee Amex card gets you AXON awards. Check this thread for the importance of those awards. I generally count on decent Hilton properties running 50K HHonors points a night so getting the total up over 200K on cards is critical because I think it's difficult to accumulate 50K points on stays unless you can charge off or get reimbursed for stays at really expensive properties.

Unfortunately, the Wyndham promo was just available to those who got a specific email with a link through which reservations had to be made to qualify. I'm not certain that the email was strictly targeted as I later received a general email that also included the link. I think in this instance, it was just critical to be on their email list at the time the promo was started.

I'm a member of Best Western's program, and they ran a stay three, get one free promo earlier this year. Given I was trying to earn some Club Carlson, Choice, and Priority Club points earlier this year, I really haven't explored them as much, but that promo seemed a good earning opportuinty.

I took advantage of the Club Carlson promotions last winter and this summer to accumulate over 200K points with an eye to using these points at expensive European big city properties in the next two years. I haven't stayed in any of them yet to give you an idea of whether the redemptions would be worthwhile although my time in the CC forum has suggested that a lot of folks have had a hit-or-miss experience. I'm not overwhelmed by CC's properties in the US. CC has been a hot new player in hotel promotions the last nine months or so, but it may very well be that the big shots have been fired. I'd still keep an eye on them for the return of any promos that earn 50K per night, however. CC's redemption levels are all over the charts: there's a property on International Drive in Orlando that has run at a 9K/night redemption for quite some time, even during peak tourist periods, while tons of their properties (including a Country Inn & Suites near my home in Virginia Beach) run from 44-50K/night, no matter the season.

Hyatt had the reputation you talk about when they ran their Faster Free Night promotions. Hyatt might be a little ahead of CC in cooling down promos, however, as it has been about two years since they've run this particular promotion.

Regarding the expiration of Choice points, I agree it's an issue to think about. On the other hand, a lot of the free night promotions run by other chains put a six-month or one-year deadline on the use of the free night. In addition, the best feature of the Choice program is that while other chains may offer a standard redemption room for one points price, they may offer other available and better rooms at a much higher level (Hilton is terrible with this, by the way). With Choice, all available rooms in the hotel go for the same applicable redemption rate for that date.

The bigger issue with Choice for me is that their point valuations can change dramatically. A lot of the European properties that run at 8K during certain times of the year may jump to 25K at other times of the year so before investing heavily in stays with Choice, it's a good idea to get to know the rhythms of those point swings.

I'm sure you won't be too surprised when I suggest that you join any and all hotel programs that might have properties where you're going to be doing your work and then keep an eye on each of their respective forums here at FT to see what hot new promos might be coming down the pike. The hotel game is slightly different from the flight game in the sense that the alliances and partners are kind of already there and obvious (HHonors points usable at Hiltons, Hamptons, and HGIs) but no alliances across brands that would allow the use of HHonors points at SPG, for instance, unlike the airlines where AS miles can be used on AA and other partners.