A Couple of Practical Questions

Swim in the top! If it's super loose you may want to think about a tighter top to reduce drag.

Don't sit down! Just kick off your bike shoes and slide into your run shoes. Easy peasy. There are many "elastic" shoelace products that you can put in your running shoes so you won't have to spend any time tying the laces. Just be sure to practice with them in a few times as they usually need to be adjusted a few times. Or if you're like me, just keep your shoelaces tied at all times, double-knotted. I just slip my feet in and out of my running shoes without tying or untying anything.

If you can get a speed suit to put on over your two piece or get a one piece tri suit would be the best two options, if that isn't practical just swim in the two piece but it will be slower than swimming in just swim shorts. I picked up an inexpensive speed suit for I think $40 when SL3S had a sale, I"m sure it's not as good as the $300 Blue Seventy but I'm pretty sure the expensive one isn't 5 x better than the one I have. 

What I do for T2 is remove my feet from the shoes 1/2 mile or so before I get to T2 and ride with my feet on top of the shoes. In transition I bend over and just slide my shoes on. I don't use socks generally speaking. If I were using socks I would probably sit down to put them and the shoes on. 

The most important thing you can do is to just go out and have fun.

A tri top should fit very snug and should not restrict your swimming ability at all, definitely swim in it. As you stated it is very difficult to get a tri top on when you are wet.

I don't sit to change shoes, just squat down to tie. I am not a fan of the elastic laces, some are, they are fast but I find them uncomfortable. 

Sit on a bucket to put your shoes on.....take in the sights and sounds, have fun!  If you can run you'll pass most of the folks who are in a big hurry anyway.  If you can't run, you weren't going to catch them anyway.

1. Swim in the top

2. in T1, just slide your bike shoes on and fasten. (flying mount if you want to get crazy but please practice first). In T2, roll in with your feet already out of your bike shoes as already mentioned. Step off the bike, run to the rack and just slide your shoes on and tie. Speed laces can help a ton here if you're trying to save time. I race in Zoot Ultra TTs and Kiawe's, both of which have a super simple speed lacing system. They're also revamping the Ultra Race to have a soft boa system with the boa dial on the side of the shoe. Also, baby powder in your cycling and run shoes (if going sockless) can help big time getting them on.

3. maybe yes but possibly no

Try the top out in your next swim work out and see how it feels.  If it's too loose as previously mentioned you have time to find another one.

If you are going to go with the bucket idea LB needs to elaborate a little more on his technique.  I'm pretty sure there's a sandwich or oreo's involved and holding court with anyone who will listen.

I was that guy. You'll adapt. Just work them into your running routine here and there. Of, if you don't care about finishing time, just continue to be that guy. Nothing wrong with that either. 

Exactly right.  I don't care for oreo's that much on race day, but I'll wolf down a ham sammiy before a bike ride on any day.  I like the home depot buckets.  They are brightly colored so it makes them easy to see in transition, and the plastic handle that is molded out on both ends makes it easy to hook on the bike handlebars.  Most of the socializing is done pre-race, and no matter what you hear or think, while everyone else is on their feet talking about all of their triathlon exploits, I can easily catch more than one looking at my bucket longingly as I sit there nodding off.....completely relaxed and uninterested.  I've got a call into the coporate office of Home Depot regarding a possible sponsorship deal......I'll keep you posted..

You forgot to mention the 5-10 balloons you need to tie to the bucket handle so you can quickly find your bike in T1. Any time lost by sitting casually on the bucket will be saved in the event you have a need for a bathroom in T1, just turn the bucket over and save all that time waiting in line for a smelly port a jon. 

Bro - why you gotta give up my balloon secret?

Get some elastic laces....get them to the perfect tightness.  Then you can slip your shoes on in T2 and have them just where you want them.

I had regular laces for my first race and quickly realized just how inefficient tying laces in a race is.

Really? I think putting on a tri top over wet skin takes a significant amount of time (and effort!)

You are clearly not taking yourself, or your race, seriously enough.  With a little work, and a few no-shows, you could win your AG someday.

At least you have T2 to build on....I don't even have that anymore.