Great analysis, OP. I have to confess to approaching this whole matter of hotel point accumulation in a much less sophisticated way, though, although it involves a good degree of advance planning. About a year or two in advance, I pick the combination of nice hotels and places my wife and I would like to go, run these recommendations by her (she's a take-charge person in a lot of ways, but when it comes to travel lets me take the lead) and tend to concentrate our business and personal cc spending and business travel accordingly. It's supplemented by signing up for good credit card deals when available, regardless of who's offering them.

For a while, the places and hotels we particularly wanted to go to tended to be Starwood-oriented. In recent years, it's been more HH, though with a smattering of other chains (Starwood, Hyatt, IC). Given the changes in the HH program and some future trips we have in mind, we might yet lean back towards Starwood in coming years, but that remains to be seen.

Not very scientific, and certainly not for everyone. But I just thought I'd mention it.

Now, having run through all that, I would suggest you take a good look at Starwood and it's cash plus points option. It often adds up to great deals, translated into dollars and cents terms. Sometimes available for great properties, sometimes not. HH is trying to replicate it, but it's unclear how widespread or effective that effort will be.