not dumb....and you will get an array of answers....

Many people will ask nicely for an upgrade...i generally do not unless i am someplace really special...IMO if the T & Cs of the MR program call for an upgrade to the ' best available room....' then i would hope that they would follow the program. If I get a particularly lousy room then i will go back and ask for something better......

As for a JW, well you don't say which one......but for example, at the JW in DC I would expect at least a nice CL room with a view of Penna Ave (if such a thing exists..) [Incidentally some of that hotel's desk staff was rather rude to me a few weeks ago when i wanted to see a room. I had to play the DYKWIA card-which i really don't like to do-and was a little bummed to see that their rooms are well, rather dull....YMMV. Stayed at the Mayflower instead and wound up with a nice, albeit in need of some TLC, suite...]