What is the big deal about all of this? If someone wants to put together a gathering of FT'rs for a weekend in whatever city, then go for it. If someone wants to have a private gathering for a few of his/her friends in whatever city, then go for it. I have been to small public dinner parties, large events such as the PIP in Hawaii, small private dinner parties, and just getting together with friends to drink.
No one is going to tell me where I have to be on a certain weekend and who I have to have dinner with or drink with, I will make that decision. For example, there will be a gathering of FT'rs the last weekend in July in both PDX and YYZ. I personally am going to PDX because I went last year and want to attend again this year. There might only be 4 or 5 people but it is ok. If it wasn't for PDX, I might have decided to go to YYZ. My decision is not based on Sean or the distance, it is just that I enjoyed the Portland BeerFest and want to go back. I miss seeing SXJ. I happened to be in YYZ last week and invited Sean to dinner and to hang out but he was busy.
As for the Chicago events, even though I don't personally like the larger events, I am still going to Chicago to see Anna and her city. I might not go to every dinner with everyone but I will still be there and will have fun. I will also be going to Seattle as I haven't missed one yet and I have a lot of friends up there, both FT'rs and not.
To me, it doesn't matter if there is something going on every weekend or not. It is up to me to choose what I want to do with my time and money. I have made a lot of good friends on FT and love to get together with them during the year for dinner and drinks. I also have been to a few private parties and have also have not been invited to a few private parties. I still sleep at night.
I think that we need to just stop worrying about who we might offend or who we might run into at an event and just get on with our lives.