I don't think you should enter any lottos at all. Just get them from TKTS or something if you make it on time. I can totally get to Times Sq at 1pm from LGA if I land at noon, but then you may not know the city that well and remember that flights can be delayed, so if you win a lotto and some of them you have to pay in advance, it sounds like a terrible idea. Get tickets in person last minute.
"People have their opinions and that doesn't mean that their opinions are wrong or right. I just take it with a grain of salt because opinions are like as*holes, everyone has one".
-Felicia Finley-