As far as your first question, I raced the half in Orlando last year and several sprints as well. I wear a two piece kit. Tri shorts and a tri top by Louis Garneau. I would have probably opted for a one piece suit but I have a hard time fitting comfortably in one. I wear medium size shorts but a large to extra large top. These clothes are obviously designed for the ultra fit elite triatlete's body which mine is DEFINATELY not. The tri shorts are super comfortable and feel great on the bike as well. I wore the top during the swim and do not wear a sppedsuit over that. If it's cold and wetsuits are permitted, wear your top and bottom under the wetsuit and after the swim just peel off the suit and go. You are also correct that ipods and mp3's are not allowed at IM sponsored events. I'm not sure but maybe you should check into the rules prior to using one as time might not be the only penalty. You wouldn't want to rob yourself of a finisher's medal due to something like that. Good luck and I hope this helps.

2 peice, easy for changing shorts/bike pants etc when you do IM and you can pull the top up when it gets hot.

I race two pieces for no other reason as that is what my first suit was and I liked it. Maybe I'd like one piece more but why fix what isn't broken?

Whatever you're comfortable in. What do you train in? I ran the Miami Man HIM in board shorts and surf shirt- swim, bike, and run- no problems. However, it was the Mountain bike with rode tires and aerobars that got the most looks.

[quote=cmccullen]I want to be as relatively "comfortable" as possible. Is it possible to change into whatever you want given enough time? I mean, can i take off my wetsuit and get into my nice, plush biking shorts and a shirt, then take the time to get into my running shorts, leaving my bike shorts behind?[/quote]

You've answered your own question. You've set your own criteria (comfort), standards (don't care about T1/T2) times, and now you're asking to be talked out of them? Tri shorts are not comfortable for 56 mile (IMO). You can wear cycling shorts under a wetsuit, cycle then run in them (have done so several 70.3/140.6s). And no headphones, especially on the swim.

1. Forget about the headphones. I've never heard of anything getting a time penalty, but I have heard of getting a DQ. They will let you finish, but when your friends and family the results, you will have a fat DNF next to your name.

2. I'm not sure if HIM races have changing tents. However, IM distance events do. I did the Great Floridian in FL in Oct (not sure if that's the "HIM" you are referring to) and I know they didn't have changing tents. Depending on the public indecency laws, I guess you could change into whatever you want.

i was quite comfortable for HIM in tri shorts, no need to change.

i think by the time you put the miles in training, you will have toughened up your taint to deal with a tri chamois for that distance...maybe throw some lube in there just prior to going out of T1. wear a singlet under your wetsuit; it will dry in the first few miles on the bike.

(but don't waste time with a full change...you'll dry off the water, but then still be sweating so it won't be that easy to put on dry clothes anyway)

1. Most HIMs don't have changing tents. Most races will DQ you for getting nekkid in the transition area. Therefore most of the time you must be wearing under your wetsuit the shorts or tri suit in which you will complete the bike and run portions of the race.

2. Tri shorts can be very comfortable over the long haul once you get used to them. I wore tri shorts with a very thin pad through HIM and IM distances and now totally prefer them to thick padded shorts even for long ride days. You might try a pair in training, you could be surprised at how comfy they are.

3. MP3 players are not only against the rules in most races, they are a stupid and dangerous thing to wear. Do yourself and your fellow competitors a favor and learn how to swim/bike/run without depending on your portable tunes.

No tunes, you'll be a danger to yourself and others on the course.
I'm a two piece fan. Easier for pit stops and more flexibility to adjust tops to different weather conditions.
What I've done for comfort in HIMs is to wear my tri shorts under my wetsuit, then pull on my bike shorts over it in T-1, then strip off the bike shorts in T-2 before the run.
As for wearing a top under the wetsuit, I'll go that route if it's reasonably warm out... slightly damp for the first few miles isn't a bother if the weather's ok. But if it's colder, I'll take the 30 seconds to slip a top on in T-1.