It's important to remind the folks at the front desk that you have status.

Many on these boards are uncomfortable asking for an upgraded room. They feel that Starwood should be proactive on this issue. Since we know they're not, it's up to us to gently remind the clerk about our status.

Here's a suggest... When you check-in, just say (with a nice smile), how does this property take care of (gold/platinum). At this point, you're half way there.
I've found that in the past, this gets you a better room. YMMV.

Ask, and you should/may receive.
Don't ask? Don't get.