Need some ideas on transition area setup.

Main thing in transition is minimize. 

You'll probably have space about the size of a small bath towel or bathmat.

You should have just the things you need during the race, plus maybe a hand towel and/or squirt bottle to clean your feet off.  Don't plan to eat or drink in transition, do that while you're biking ro running.  Spare anything sitting around is just a distraction--if you don't know you're going to use it, stick it back in your bag.  Same with things you'll want after the race--keep them in the bag.

If you're going to put a shirt on in T1 and not wear it for the swim, then I'd say whichever is looser and easier to pull on over a wet body--probably the running shirt. 

Bottle on the bike is good, but I'd think twice about freezing it.  You need the fluid more than you need the cold, and if it doesn't thaw as much as you think it will you could be screwed.  Refrigerated or even room temp will be fine.

Second bottle for the du is your call, but if you get some fluids in during the bike and there are aid stations on the run course, do you really need it for the second run?  If you do, again, don't take a drink in transition, just grab it and go.

I don't usually practice transitions at full speed (although I probably should), but I do lay out my stuff the night before the race and walk through all of the steps.  Helps mentally, plus right after I do that I pack up my bag, so I'm sure I've got everything.

I usually bike without socks so I don't have to worry quite as much about getting my feet squeaky clean--usually most of the grit comes off by the end of the bike leg.  I find putting a little bit of BodyGlide just inside the heel makes the bike shoes slip on a little easier.

I can't run without socks, though.  Quickest to put them on before the race and roll them down your foot so you can just stick your toe in and then roll them up.

What was the distance of that race? Was there a final decision that changing tents would not fit in transition? That is a lot of stuff to get kicked around. The bags have to go!