Yes, all the time, all browsers.
I tried checked three sections to confirm this bug. In both cases, I was searching for the user "$ilent" (and I hope he doesn't mind me naming him :)):
1) When composing a PM, if you begin typing into the "TO" field, it autocompletes names for you (so if you entered "zoda", you would see my name, and two others). However, at no stage when I was typing out "$ilent" was I suggested his name.
2) When searching for users (search bar at the top of any page, then going to "User" tab), searching for "$", "$i" up to "$ilen" gave no result in the "User" tab. Only when I fully typed in "$ilent" did I get a match (note, for the PM bug above, even typing in the full name gave no suggestion).
3) His profile URL doesn't include the symbol:
I expected the search results to act the same as if I was entering any other username.
Since we no longer have a "member's list" as we did on vB, I don't have a list of usernames with uncommon symbols to create a list. All I can confirm is the $ is one of them.
Windows 7 x64 Professional