I am a Loews member and I have always gotten an upgrade. When I first joined Loews as a blue member I always got upgrades at the HRH, usually from garden to pool view, once from pool view to concierge and once from pool view to deluxe pool view.
As a gold member (two more stays to platinum!) I have gotten a $35 upgrade to the kid's suite (with an entertainment code discount rate) and more recently was upgraded at the Royal Pacific from a standard room to a king suite for free at a $99 a night rate. **The ugrade to the kid's suite came one night into our trip. When I inquired the desk clerk said "I have nothing for you tonight but tomorrow I can move you to a kid's suite for $35" I said YES! and we moved the next day.
I have found from personal experience several things:
1. Sometimes checking in later in the day HELPS. When you check in early they look at all the "expected" check outs and if you have a standard garden view booked they will look at those rooms (and naturally find plenty that will be available). Later in the day the pool of "available" rooms is smaller.
2. I always call ahead and very NICELY speak with a reservationist and ask him or her to write down my requests for upgrade, I give her my member number and requests for milk and cookies, USA today, etc.
3. When we arrive I make pleasant conversation with the desk clerks (not hard to do since they are generally a great group of hard working young adults). Last time, at the Royal Pacific, the clerk was a former employee of the AKL at disney and my husband recognized him from our stay there in April. He was awesome! But I have found that great kindness, small talk and a upbeat attitude goes a long way with people used to dealing with demanding people. (and lets face it...desk clerks at hotels get a LOT of complaints "my bill is WRONG" "my room is not right", etc. etc.
4. Remember them if you return. At the HRH I was talking to a women working the desk. She had a northern accent and we got to talking about Boston. I told her my boys were going to camp in Portland, Maine and she gave me the number of her friend who managed a hotel there. I called and got a room at a sold out hotel during camp parent's weekend. Next time I went I sought her out to thank her.
We should start a thread detailing Loew's upgrade stories. I bet there a lot of people with great upgrades to talk about!