The upgrades at PPH seem to be hit or miss, but you might have a good shot at it. How early will you be arriving? In other words, will you go to the hotel first to leave your bags and check in at the front desk before the room is actually ready?
For some reason, I got very lucky and was upgraded to a view room at the PPH 4 years in a row -- although some view rooms were better than others. Other people have never been upgraded. There seems to be no real rhyme or reason to it. I've never asked for an upgrade, but I just got them.
I really think a lot of it has to do with the specific CM who checks you in, what kind of mood he or she is in that day, how booked (or not booked) the hotel is that day, if it's a super busy week in general, how long you are staying (shorter trips have a better chance of upgrades, I think), and, of course, timing and luck. I have always gotten to the hotel super, super early in the morning too, so I could get all of my paperwork and things taken care of before a line formed at the front desk. So maybe arriving early helped, although I have read about other people's upgrades that happened in the afternoon.
Did you book PPH online? It might not hurt to call Disney's Reservations before your trip and have them make a note on your file that you are celebrating your 10th anniversary. Otherwise, mention it when you check in, for sure -- but don't come across as though you are trying to get something, as that will probably work against you!
Are you only interested in eating in
Disneyland, or anywhere in the whole resort? You could try Steakhouse 55 at the Disneyland Hotel... or Napa Rose at the GCH... or Carthay Circle in DCA... Blue Bayou in Disneyland. Those are all good "special occasion" sorts of restaurants.