how do HIM transitions work?

The transitions are like that of smaller events. Just a lot more people around since it's MDot. Something is off if you need to use more than just a tri suit for a HIM.

How long have you been using that saddle? It can take some time for you body to get used to a split saddle. Things are working down there that haven't been before. I'm also wondering if it's actually your sit bones as I found the Max to be overly soft/squishy with padding.

Not sure why you are asking if you know you can't...? What am I missing?

You can get disqualified for changing in the nude can't you? haha

Maybe it does just come down to more time on the Cobb. I hope I get used to it by race day then :p it feels like heaven on my cycling bibs but with the thinner padding on my tri suit it gets to me after about 30mi and I start having to stretch out every 5-10min or so. Had it for maybe a month or so, put in maybe 2-300mi on it.

Actually you can, sort of.

For IM I did, T1 was large with changing tents too far away and I wanted to wear my bibs for bike.  T2 was the same layout.

I wore a pair of Nike Pros which are thin compression type shorts throughout the event.  I wore just them under my wetsuit.  Pulled my bibs on over them.  Cycling with them under the bibs did not create any comfort issues.  In T2, I pulled bibs off and pulled running shorts over them.  It worked out very well for me.

it's not too late to get a better saddle for you.

I gave up on that same saddle, couldn't ride it comfortably for more than 40 miles with cushy riding shorts. So I switched to a Specialized Romin Evo comp Gel...I love it. Now this is on my Roadie, but I'm sure it would be ok on my tri bike too.

On my tri bike I have a Adamo Prologue, which is fine.

You might spend a little time now fixing the saddle problem and you'll be happier and can just wear a tri suit for the whole race.

Just get a good pair of tri shorts and do the whole thing on them. Don't make it more complicated than what it is.

Now, if you MUST wear the bibs, you can do the swim in jammers or running short tights and just put the bibs on top of them at transition so you don't get disqualified (and put in the sex offenders list) for being nude. 

I do the same.....easy as can be.

Yup.

As to the bolded part...

I wouldn't count on it.  While saddles are certainly highly individual, the Romin Evo saddles just aren't very aero position friendly.  Awesome road saddle though.

I tested about a half dozen saddles last year - Adamo Road, Adamo Race, Cobb V-Flow Max, Cobb V-Flow Plus, Specialized Romin EVO, Fizik Arione Tri 2.  The Romin EVO was the best feeling saddle in the road position and the absolute worst in the aero position.  And I was very careful to setup each saddle and do multiple rides with each.

Do a search on Slowtwitch for Romin EVO and read about people's experiences.  Everyone says the same thing - great road saddle, horrible tri saddle.  I think it was Paulo Sousa that summed up the Romin EVO on a tri bike the best - "Many have tried, none have succeeded."

That's my plan too. I don't care for my tri-shorts and I don't feel like buying another pair.  I'll wear only the compression type shorts during the run, though. I train in them.

4:45's pretty fast! Hope your bike and run are up to par. 

At that paces, you really should have your transition down smoothly. Do 1 or 2 sprints or olys before for practice - it's exactly the same.

A trisuit is what you want. No wasting time changing in and out of stuff.  4:45 is fast enough that unless you know you're one of the top cyclists/runners and have a solid swim, you'll need your transition minutes. The trisuit goes under your wetsuit no problem. 

23mph is a pretty studly HIM bike! Might I ask how you came up with that estimate?

Curious, because I'm only a hair better on the run than the bike (I'm actually dead equal in race placements for sprint/oly, but HIM I'm a bit better on the run), and I run about a 7:20/mi on the HIM run, but am only about 20.5 for the bike in a HIM.

Curious on this one too. Even on a flat course, that's generally considered rather fast.

i feel like there is a story here.

fast-ish i would think, but not "faster" than a 7:20 pace on the run right?  i'm looking to pace 20+ on my HIM, wouldn't think that would be considered "fast" on flat course.