My thoughts....
1. What would you say about mid to late september?
I'm okay with that time frame.
2. Duration?
IMO, late morning, say 11:00am - 5:00pm with a break for lunch, or catered lunch, then an after 5 event for those who want to hang out, while others that want to get back home could vamoose.
3. Weekday or weekend?
I am ambivalent. Fridays would be bad for me, I really enjoy watching my high schooler play ball. Other days I could take off, though, and saturday would be fine with me, as long as there was not something insane going on in Chicago on that day.
4. Potential topics to discuss? Speakers?
Potential topics, hmmm:
"Monitizing the .TV Extension"
"Brand vs. Product Roundtable discussion"
"Why Buy .TV? How To Market .TV To Endusers."
Those are 3 ideas, speakers, no clue, though we could probably get someone from shareasale to speak about their merchant's product videos.
5. Would meeting at shareasale be okay with everyone?
They are downtown chicago, parking will set you back twenty bucks, but I like the idea of getting a conference room for free.
6. Anyone want an after hours kind of event, like a ball game or something? Anything going on of interest in Chicago during mid september? Any conflicts? No idea.