This might be the most extreme ever resurrection of a dead thread but earlier this year I encountered this same problem at a Hilton property. We were there for 5 nights with ~6 devices including a Roku and I probably spend a total of an hour or more over the course of the stay just logging everything back in. It was enough that I knew I wouldn't book at that property the next year (it's an annual trip) so I wrote to Hilton Corporate about it. This was a few months ago but today I got a very nice call back and long story short they've been rolling out a new centralized authentication platform that defaults to 7 days of access. They've done 2900 properties so far and have another 2100 to go. I was impressed to hear that they (Hilton coporate and IT) have had to go through the same thing when they stay in their own properties so it's something they've been aware of and are finally solving. I haven't yet stayed in a Hilton property since the rollout began but if others have experienced it I'd love to hear how it worked!