Will you have a car? Is there a certain age crowd you'd like to watch? :)
Here's a couple to consider:
1) Parkside on 6th street
- This is the heart of 6th street with lots of live music near by but note most bars in the area are geared toward college students.
2) Perlas on South Congress
- lots of shops in this area to visit. Sitting outside(out front) will provide plenty of people watching.
That sounds perfect. I'm following your routine next Sunday.
In response to the more general question, I like rolling up to the Wink wine bar, ordering some truffle mac and cheese, and making new friends.
And while I actually like parkside, I loathe the people watching on 6th, though I also can't watch more than five minutes of Jersey Shore.