I'd highly suggest making the Lawrenceville neighborhood your base. There's a Tryp Hotel there and probably some Air BnBs. Walkable neighborhood with TONS of restaurants, bars, bakeries, coffee shops, breweries, etc., etc. LOTS to do, very walkable. Skews older. Definitely a hipster neighborhood, but again it's a great base and you can walk to all these things.

Go to Phipps. It'll be their Orchid and Bonsai show, which is fantastic. You can couple it with some outdoor ice skating in Schenley Park (tip: they have an adult only skate Friday and Saturday nights). Lots of fun. Millvale has a great record store in the Attic, if that's your thing. Millvale also has a couple breweries and really cool little haunt in the Whisper Nest.