Is now a bad time to be sending out requests? I've always been curious if people would rather be left alone this time of year but haven't really sent out enough requests on a consistent basis to tell if successes are less likely during the holidays.
I've been researching TTM over the past 4 months, but haven't personally sent out any requests. On that note, I feel I can still answer this question decently.
If you send right now, you are probably fine. I'd expect the retired players to be a little easier to acquire, but that's just my opinion. I'm planning on sending my batch out right after Christmas and I suggest the same.
Really all depends on the person, if they don't want to sign at this time of the year odds are they don't want to sign at anytime of the year. Its not like you are showing up at a family Christmas party or something asking for an autograph. If they have the time to sign then they have the time. If anything it might take a little longer for the mail to be sent both ways but unless the person is traveling for the holidays I wouldn't see it mattering. Who knows there could be people that enjoy going through fan mail more at this time of the year if they don't have their families around to enjoy the holidays with. I'm sending out 5 (maybe more depending if I want to write anymore letters) today