Just dropping some suggestions in here. I live/work/entertain myself in the city -
NORTHSIDE (PIRATES/STEELERS)
Monterrey Pub is probably my favorite bar in the city. It's on Monterrey Ave off of North Ave in Northside. I think it has the best burger in town and it has a small scratch made menu of some really awesome food and my style of beer (nitro Guinness, Eichenberg, Smithwicks)
Western Ave in Northside has some good bars restaurants. Allegheny Sandwich Shoppe is meh, but you can get breakfast and lunch there during the week. If you want breakfast, Lindo's on Western is really solid. My favorite Peppi's in the city is also on Western. There are now breweries (Four Points and 412) and a wine tasting room (Refucilo) on Western. Across the street you'll have Nicky's Thai (which is probably the most popular Thai spot in Pittsburgh) along with Modern Cafe (great drinking bar) and a new bar going into called Tony's Pub.
Legends on North Ave is a great place to get a good meal.
If you are in town on a Wednesday, the most underrated event in the city is Banjo Night at the Allegheny Elks on Cedar Ave. It's a ton of fun. Drinks are cheap and the old timers play music. The vibe is awesome. You can also drink there without a membership 4 hours before games on Sunday's.
Penn Brewery is also an underrated place to go before any game. The food is really good and I love the beers.
UPTOWN (PENS)
I'm a season ticket holder/Duquesne graduate, and Souper Bowl is my go-to like many others. It's where EVERYONE drinks before the game. What may people don't know is that their food is actually really good. If you want to grab dinner after a game to let things calm down, I recommend stopping here.
Cafe on 5th is just like Souper Bowl. Great place to drink at before a game. I'm not a fan of their food - it's been miss well more than it has been a hit.
Parking hack - There is a lot through the alley way next to Mitchell's on Ross St. The alley way doesn't have a street name that I know of, but parking back there is $10 and it gives you the quickest access to the highway after the game.
STRIP DISTRICT/DOWNTOWN
I think Roland's is a really fun place to take in a game and though I'm not a gigantic fan of their food, their munchies are pretty good. Roland's is a spot I have taken in many Steelers games, and the environment is always fun.
Luke Wholey's has great food. Their menu changes, so check it out before you go in.
Ciopino has great food for a nice dinner out, and a bonus if you're a cigar smoker. They have a nice selection of bourbon and their cigar prices won't kill you. Hack - you can also pick cigars up at Leaf and Bean if you want a larger selection.
Eleven/Kaya - I lump these together because they are both Big Burrito restaurant group and things are similar - good happy hour and really solid food, IMO. Eleven is upscale, Kaya is Carribean.
I think Cinderlands Warehouse is a gem. I love their beers, and their food is quirky but always awesome. I'd recommend this place to anyone that comes into the city.
Coup Deville is probably a great place to pregame or take in a game, I'd imagine. I haven't done so yet, but the couple times I have gone in, it seems like it could be really fun.
DOWNTOWN
The Eagle is probably one of my favorite spots in the city right now. Awesome food.
The Warren is my favorite cocktail bar in the city. Super pro bartenders. Really nice place to have a couple of really high quality drinks and their food is really good too.
Scarpino's - just ate there for the first time. Really great Italian food.
LAWRENCEVILLE/BLOOMFIELD
Not going to really give a breakdown because Lawrenceville is superior to the Southside, and is where I would recommend anyone go aside from Southside. Aside from Mike and Tony's there isn't a whole lot of redeemable qualities of the Southside.
My favorite spots in Lawrenceville are 11th Hour Brewing, Stinky's, Hop Farm, Condado Taco, Round Corner Cantina. I admittedly don't do a ton of drinking in Lawrenceville - I actually try to avoid it, but if you want concentrated wining and dining, this is where you should go.
In Bloomfield, I would recommend Lot 17 and Tessaro's.
MISC.
Sharpsburg - Dancing Gnome; Hitchhiker Brewing
Millvale - Grist House Brewing; Sidelines; Caesar's; Grant Bar; Strange Roots