Speaking purely from my point of view, there are Pros and Cons to September:
Pros:
- I could theoretically attend Zedcon 2, which is looking like it'll be in August.
- I'll be back in work six days a week in September instead of two, meaning I can spend a bit more money on this kind of thing.
- Weather will be cooling down, so if I have to spend 3-9 am walking the streets of Toronto again, it will be more bearable.
Cons:
- If I'm working six days a week, it means I'm taking time off work.
I can't think of any more cons... Pros kicks Cons ass. I vote yes to September.