i did use the boarding pass privilege once at swissotel singapore abt a year ago and didnt like the look i was being given at reception. In fact, they tried to push me into the lower floor rooms which were comparatively less desirable than the higher floor rooms.
Other than that, retailers usually are pretty good at accepting it, no questions asked.
But i do agree with the op that sometimes when u try to search for availability for the hotels, it comes up empty for a long stretch. Happen to me before taht you begin to doubt the genuiness of the offer.
Bear in mind though that SQ used to market the boarding pass privilege as a limited promotion but because its running so long, its expected to continue indefinately.
Maybe CGK, Movieman or some of our other regular krisflyer contributors could contribute their experience with the boarding pass privilege programme.