In trying to clarify what I valued most in airline elite status, I started to ask myself the same question for hotels. What matters most to me in elite status?
My travel pattern is something like 30-40 nights per year for work, and around 25-30 nights per year for leisure. Where my trip is for work, my attention is more towards convenience, facilities (like gym, laundry) and getting a good night's sleep so I can work effectively the following day. Through work I receive corporate benefits like free internet, flexibility in cancellations and complimentary or discounted breakfast.
When it's for leisure though, then my focus turns towards stress-free comfort, getting the maximum return on every penny I spend and to make a memorable experience. Luckily I am still eligible for the corporate benefits above, even though it's a private trip.
But to make the trip extra special, I have to choose my elite status and my hotels carefully, so here are my priorities:
1) Decent earning vs. redemptions ratios
Any issue of award availability is mostly mitigated by my holiday flexibility. I don't tend to have any problem spending any points I have, bar a handful of occasions. I tend to rely on combinations of promotions such as IHG's Big Win plus Points Break to truly maximise the value.
2) Early check in and/or late check out
To save on holiday expenses I often find myself taking overnight buses or flights. Most of the time this will involve an early check in or late check out to accompany it. My percentage of successful late check out requests have been fairly mediocre in recent times, though early check in has been fairly good somewhere around 80% I reckon. Simply, it comes to having a comfortable bed to get an extra daytime snooze.
3) Room upgrade
This probably divides many people, but suite upgrades and getting into swanky rooms really doesn't interest me that much, mainly because it's so unreliable, even with Starwood Platinum. When I first started this hobby a few years ago I used to be ultra-obsessed. But as upgrade after upgrade failed, I stopped bothering and actually enjoyed my hotel experience just fine.
I'd be interested to hear from your priorities and why. Maybe you might influence me to rethink my own strategy!