I'll try to answer, but my races were slightly different.
1) Depends when you need that bag and if you can enter transition the next day after you've already checked in the bag. I've never had a transition area setup that took place the night before so I'm not sure about this one. If you can enter the transition area about 30 minutes to an hour before the race, you can dump everything then and grab it as you're completing final setup.
2) Pin to your jersey - just one pin will suffice as long as you have it when you cross the finish line (that's usually what the race people tell me, although you probably won't be easily identified for any pictures that they take). I usually just pin (securely) to my tri-suit for the swim too so I don't have to think about it.
3) If you have one of those thermal lunch bags, take a couple of ice packs and pre-mix the drink. It kept my drink icy during 98 degree weather. That way you don't have to think about it during transition either.
4) What do you mean special needs bag?
5) The less you need to think about during transition, the better and faster your race will be. You're already going to be nervous, so keeping it simple is your best bet. Lay everything out where you can easily see and reach it and just concentrate on racing.
Good luck!






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