The North Side is undergoing a bit of a renaissance-- I think you will be pleasantly surprised! It's my neighborhood so I will just make suggestions in the area:
1. Acanthus (www.acanthus.biz) for a serious meal. Make sure to go to the library bar for cocktails even if you don't eat there. It's worth it just to see the gorgeous renovation they have done on the Boggs Mansion.
2. Muriel's Cafe on Western Ave. (www.muriels.net
)3. Sassy Marie's on James St., where the James St. tavern used to be. (www.sassymaries.com
)4. New Moon Fusion Cafe over by PNC Park on General Robinson St.
5. Richard's Smokehouse for takeout BBQ on Brighton Rd. Cal ahead because they have the weirdest hours
6. Go north about 5 miles and hit Vivo in Bellevue.
There are also a couple new coffeehouses on the North Side. One is Beleza and the other I can't remember!
I'll let other hounds recommend places in their neighborhoods.