There are plenty of great places around the city. Many breweries, Hofrabau being just one of the many. Penn Brew, East End, Roundabout, Hop Farm, Draai Laag, all fairly accessible and worthy stops. OTB, Pipers are cool spots in the Southside as well. That said, I try avoid the South Side like the plague. That doesn't mean I wouldn't meet there though. Other good potential places could be Bloomfield Bridge Tavern, Harp and Fiddle in the strip, Round Corner Cantina in Lawrenceville, Kellys Bar and Lounge in the east end, Sidelines in Millvale, and the list goes on and on. I'm open to suggestions, but I'd say it's about time that something happens.
The main reason I mentioned my place is that I have lots of space there, a nice fire pit, and I live two blocks from Roundabout Brewery as well as a host of other bars and restaurants. Easy in and out for everybody and should anybody find themselves too intoxicated I have room to keep bikes safely (inside and behind a locked door) and even couch space should that be needed. This could be planned as an after stop perhaps, rather than the initial meet up, because like you have said perhaps it's best to meet more casually.