Usually the outlet items are lesser quality. It isn't the same. The labels aren't even the same as the originals. If you're going that route, I'd be upfront about it.
I aim to start soliciting donations 5-6 months ahead at least. Some places specifically require a year out, some 2 to 3 months, some 8 to 10 weeks so it varies.
No, I'm in Orlando and March,April,May is gala season here. Almost EVERY organization/school is having one so we try to get ours in early so we can get ahead of the others. We're already scheduled for March 14.
I know what you mean about spinning your wheels. We sent letters in Nov and I started making follow-up calls in Jan. and no one could remember getting/reading my letter. I'm thinking maybe I'll do online requests in Sept/October and then email/phone/mail/in-person asks starting Jan.