I grew up in Racine just moved away a few years ago. Sorry I missed the thread, been busy at work and not checking the forum as much anymore...
Curious where you ended up? My two cents in case you are there again...
Break and Run is a small pool hall in Racine, I was only there a few times it's ok. If I remember owned by an older couple that weren't overly friendly the few times I was there and equipment was so-so.
Boomers as Mark mentioned is nice in Sturtevant, ok equipment (older GC's) but I like the people there and it's cheap, a few good players too who are regulars, including this past year's Wisconsin's Masters champion who I played last time I was there.
Claudio's room in Kenosha if it's still open would be okay, I don't know that I'd personally go as far as saying it's a "true" pool hall, it's a small room owned by a good pool player. I remember there always being a lot of kids in there (no alcohol), but there were definitely some decent Kenosha players hanging out there as well and Claudio was always nice.
Romine's is still the place to play in the area, nice consistent equipment with frequently changed cloth, large selection (50+ tables) and as mentioned two nice billiard tables and a 6x12 Snooker table that's tight as hell... I traveled back to Wisconsin about a half dozen times over the last year for work and went to Romine's every time with a few stops at Boomer's as well. I don't think they've gone that far downhill, the things Ed mentioned have been that way since I've been going there 15+ years ago. The kids have taken over the business now, things have aged and don't look as "new" as they once did, poker tables and events have taken up a predominant place in the room, but they still have great in house leagues with some decent competition, a nice Friday night tournament, and a good in house Mexican restaurant. And if you are looking for a date you know what nights to go...
Scott