Downtown and walking. Only there for a day of business and then a day of shenanigans.
I don't think there's really any "can't miss" stuff but I'll give you some suggestions. The below is assuming "downtown" is near 6th and Liberty.
If you're going to do some breweries on your shenanigan day while walking then I think you have 3 options:
1. Do the North Side/Shore breweries which consist of: Southern Tier, Voodoo, Four Points, Late Addition (formerly 412), Allegheny City, and Penn Brewery. This area of town actually used to be a separate city (Allegheny) and has some cool architecture in the Mexican War Streets. If you're over this way there are also some artsy museums you can check out (Warhol or Mattress Factory).
2. Do the Strip District breweries which consist of: Helltown, Aslin, Bonafide, and Cinderlands. The Strip District has a bunch of interesting shops. They were mostly local but now it's getting a bit more corporate. Anyway, I'm sure you'll see some neat yinzer stuff in this neighborhood.
3. Do the Southside breweries which consist of: Burghers Brewing, Sly Fox, Fat Head's, Velum, and Levity. I'd actually suggest getting and Uber/Lyft to Levity and working your way back towards downtown. Levity's area is the Southside Works which has the Cheesecake Factory in it and restaurants with some similar vibes. I swear it gets more local/yinzery once you leave the Works and head towards the lower numbered streets.
Restaurant-wise I'd just say to do a Google Map search for the type of food you're looking for. Anything above 4 stars should be pretty decent. And 4.5 stars or more should be quite good. One of my go to restaurants is Kaya in the Strip.
Why the f*** are there so many furries
Furry convention is this weekend.