I'm assuming it's an open water swim? If so, and considering your current pool/race pace, I would go for the slower group and try start at the front.

Yes it is a Sea water swim, wet suit legal.
because I am on the Cusp, I thought If I can swim on slightly faster groups feet this will pull me along :-)
I am I guess wondering whether better to "pull" a slower group, or sit on the feet of people that are slightly too fast.

On Average How much time should I Benefit with wet suit swim in Salt water?

And also As I think About that, Is there any benefit to swimming longer sets at my Hopeful race pace (Sub 38mins) using a pully in the pool?

How comfortable are you with contact in open water? Personally, the swim is my weakest leg, and the bike is my strongest, and I am very uncomfortable with the contact with other swimmers in open water. I would chose the slower wave to minimize my contact with other swimmers, then rely on my fast transitions and bike skills to make up for it. If you don't mind all of the contact, though, the answer would probably change.

If you chose the faster swim group, better swimmers will be swimming over top of you.
Personally, passing ppl on the bike is good for ego, and a less stressful than having stronger swimmers overtaking/kicking me.

Thanks for the Feedback.
I appreciate this and will take it into consideration. It seems the wise thing is to start in slower group.
(Out of Curiosity - swimming about 40Min for the swim would put me well into the bottom quarter of the swim right?)
My Bike is currently expected to be around 2Hr20Min - so I imagine will need to Pass quite a large number of people on the ride.

You said salt water, is it an ocean swim or in a protected bay/cove? Based on the times you mentioned previously, and the fact that you said you don't expect to see much improvement from now until race day, I'd be surprised if you go sub-40. I wouldn't at all be surprised if you are in the 41-42 min window and to go under 38 would be a great swim considering your previous swims. Granted, I could be wrong and sometimes the stars do actually align for a great swim, but a 38:00 is a 1:58 average per 100m and based on your previous swims that's a pretty big improvement, even with a wetsuit. You will need to swim the perfect line, have good clean water the entire way, and the course will need to actually be 1.2 miles and not long (which they always are). Not trying to be ass, just being honest.

Sounds like you want to go with the faster group. I'd go for it, love proving people wrong. What's the worst that could happen? I'd rather be at the back of a pack than in front of one knowing that I'm going to catch them after transition. If you even have a chance of staying with the guys in the faster heat just go for it, who knows maybe you can have a great day and surprise yourself.

Keep in mind that the rolling start is continuous. There really isn't a group. Swimmers never stop entering the water. If you are in between those times then put yourself near the back of the faster group. Or the middle. It won't matter much. The rolling start really spreads things out.

I will let the rest of ST tell me if I am wrong, and I may be, but I think those are typical times for a pro male.

Start with the slower group. There are no miracles on race day

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What are you people, on dope?

—Mr. Hand

Thanks for the advice.

( I think maybe starting the slower group may be the wiser decision by the sounds of things)

As far as Conditions of the water, I believe it is a bay, so Assume the waves will be pretty small / mild.

And as far as the Bike Goes a 2hr20 puts me at average speed of around 38KM Per Hour which is the range of Training rides that I have done with my Training partners.

Thanks for everyone's input. given me something to think about.

Are you drafting off your training partners? Because that is called cheating on race day unless you are doing a draft legal race.
You might be that fast. I don't know if you come from a bike racing background that might make it possible. It just isn't likely unless the race rules allow drafting and you are comfortable riding closely with unknown riders.

No we are riding non drafting rides on our TT bikes (I mean it is possible that we get small drafts ) we not sitting and measuring the 12 Meter gap, but we are not riding in peloton either.

I am from a cycling and running background. I raced in the local Bike association for 3 years before trying my hand at triathlon.

I don't think that's unrealistic for someone with a cycling background. I know a at least 5 or 6 guys in my tri club that can and have gone sub-2:20 in a 70.3 bike.

Depending on the course, most male pros should ride in the 2:05-2:12 range. Top pros ride closer to 2:00.

My swim and bike times are similar to the OPs projected times. I typically swim ~38 min and then ride ~2:20. It's fairly common, I think, for adult onset swimmers with cycling or running backgrounds to lay down lopsided splits like these (i.e. horrendous swim splits and decent bike/run splits), simply because they have a good aerobic engine. In a typical 70.3 (i.e. not extremely hilly), dozens of age groupers ride in the 2:20 range, though very few ride 2:15.

If you're not a huge guy and are cognizant of staying in the aero position, it shouldn't take more than ~220-230 watts to go 2:20 on a flat to gently rolling course. It takes substantially more watts to go from 2:20 to 2:15 or 2:10 though.

Nice to Know I am not alone in this @Conradz
I really try so hard in the Pool and I know that it is about technique etc ...and I also know eventually it will come with time and Patience.
But Honestly is a little disheartening to Swim 4 Times a week for the past 2 Months and see little to zero improvements (I feel bit fitter but no faster)

Anyways - based on what you say, I should have a little bit of company with me during the race :-)

There seems to be some confusion in several of the posts as it sounds like they're talking about the 37:30 and 40:00 as two separate groups in the water. As someone else mentioned, this is not how it should work for a rolling start. It'll be a continuous stream of swimmers and the two expected times are just to pick an appropriate spot in that stream. In your own words "My Goal for the race is to swim 38:00min (or there about - sub 40min)"
So you yourself believe you sit firmly in the sub 40 group. You're not "on the cusp". This is very straightforward and your bike expectations should not be factored into it. Go in the sub 40 group. If your expectations rise or fall between now and the race you can choose where in that group to position yourself accordingly. If you get it wrong by starting in the middle of the sub 40 group and ending up swimming 35 that's absolutely fine and it won't cause you too much difficulty. Passing a few people is not a big deal and I would much rather pass people than have lots pass me.

A few people have made posts in the past about strategically seeding themselves dishonestly in the hope of gaining some advantage. IMO that's a dickish approach, which if it became widespread would make a mess of the whole intention of seeded rolling starts. Be honest about your expectations and choose a group accordingly. Simple. This is not a race decision you need to stress about - it's not that critical. Just don't skew things on purpose, if everyone did that it would be a mess and there's really no point.