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Roscoe Village is a part of Lakeview - so is Wrigleyville and Boystown. The goth/sex shops are really on at the corner of Belmont and Clark (the only ones I can think of anyway), and that corner is really like nothing else in the city. It's in Lakeview, BTW, which is defined by Diversey on the south, the lake on the east and Irving Park on the north. The western boundary is either Damen or Western, depending on which map you're using. Western was the boundary of the old Lakeview Township until it was annexed back in the 1910's, but on the last one I saw, Damen was the boundary. I'd say that Lakeview is best defined by either the strip of bars between Barry and Addison along Halstead that makes up Boystown or the strip of bars between Cornelia and Grace along Clark that makes up Wrigleyville. They're very different (think gay and frat boy) but only about 3 blocks apart at their closest. If you're going to live in Lakeview, you're gonig to have to deal with drunks, but you have your choice between drunks in assless chaps or backwards baseball hats.
Mal, for 1100/mo, you can pretty much make up your mind based on the building. Given that you're basically being the Golilocks of aging (these neighbors are too young, these neighbors are too old, these are juuuuust right), you're probably going to be hard to please. Go figure. However, you might try Lincoln Square, which is roughly 8 blocks in any direction from the intersections of Lincoln, Lawrence and Western. The Metra is at Ravenswood and Lawrence and can get you to Canal and Madison in about 15 minutes for about $2.50 a day (that's less than the EL). It's an old German neighborhood that's starting to turn, so the kids would tend to trend younger. The elderly either own their own homes or are moving out. There's also a little city-center area with some pretty cool shops.
You could also try North Center (Irving and Damen), but that means taking the Brown line, which is under construction and is a general pain in the ass to anyone taking it from that far out.
Joe, my best suggestions for you are either Wicker Park or Bucktown. Rents should in line with what you're looking for, and it's a pretty cool little area. It's along the Blue Line, although pretty close in, so it would probably take about a half hour to get out to O'Hare. There are lots of cool little shops and restaurants, including some of the best pizza in the city (Peace). I have several friends that own rental property around there, and from what I know about what they charge, your target range is right in what they charge. Keep on the lookout for folks that are renting out condos because you might find a good deal.
When you say you're looking in Irving Park, I assume that you mean Irving Park the neighborhood and not the street. If that's the case, I'd stay out of that neighborhood if you don't like gangs. There's definitely a criminal element out there, although it seems to be transitioning. They had a bunch of buildings go condo in the last 2 years, which is usually one of the first signs of the criminal element being forced out.
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