I concur. The Milwaukee and Baltimore properties, of the 25-30 that I've visited, are a stain on the brand name. Sometimes the 30% point bonus just isn't worth the insulting service.
I had the same reaction: Diamond doesn't mean squat, no free WSJ (and the gift shop isn't open in the early morning), and room service took forever (but the Balt. property is the all-time loser there). They also put up a fight when I tried to cash a check (I ended up paying $2.50 to the ATM next to the front desk). Here's another oddity: their coffee shop/cafe, which actually was pretty good, isn't open in the early morning!
The two Hilton properties in Milwaukee are pretty nice.