Hilton HHonors - Should I call for an upgrade?

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I am checking into the San Diego Doubletree tonight. It is my first time at this property and apparently they have 2-story suites. I would really like to try that suite but since I arrive around midnight I'm afraid the upgrade will be gone by then. Would it be ok to call the hotel this afternoon and nicely ask if they could upgrade me to that suite? I am HH Diamond. Thanks.

What I typically do in these situations is: call the hotel around noon-1pm (once most people have checked out) and tell them that I want to confirm for late arrival. I then ask if any suites are available. It's rare that I get a confirmed upgrade over the phone, as they usually say something to the effect of "I'll see what we can do for you." Most times, I will get upgraded to a suite. Whether it's because I called or because they planned on upgrading me anyway, I have no idea. Good Luck!

For future reference, for special occasions (Valentines for example) I write a letter to the GM a few weeks in advance requesting an upgrade based on the special occasion. The two times I've done this so far (ES ATL Centineal Park and Hilton LAX) I have been treated very well... the ES ATL called me last week and confirmed an upgrade to their Presidental Suite (full dining room w/ China, huge balcony for throwing parties) on 02/09, as well as chilled champagne and rose petals on the bed. The craziest part is it was a Diamond Force award stay, so they were making $0.00 and they are still going above and beyond (equal to the service the Ritz ATL gave us on our wedding night).