Gearing will be fine. You have the background experience and engine to go Sub 5. Practice nutrition in training (although 70.3 nutrition is much easier than 140.6). Don't overthink it. Just be consistent with your work and good luck.

Thanks. Fueling is something that I know I'll need to figure out. Is the swim pacing pretty much all out or do you save some back for the swim and run?

1) TP plans heavily focus on the bike, which for you is perfect. Stronger bike means a stronger run as well. 266W at 175lb puts you around 3.3 W/kg and you will probably see a good bump in FTP as a new cyclist starting structured interval training. I'd still swim 2/3x a week and use one swim day as a recovery day since a +/-2500m swim workout shouldn't be too difficult for someone of your swim pedigree. If you feel you need a full rest day that week, just drop the swim.
2) I dont know the Boulder course specifically but have raced at a similar W/kg with 36/52 11-28 gearing on hillier courses and I found it sufficient. If you're not a local, altitude could play a role on race day and is something to consider.
3) A few other things:
-Race Nutrition: very important during 70.3 races. Poor attention to this on the bike will kick your butt on the run. Practice this on long bike workouts. Typical targets are 60-90g carbs per hour but experiment and find what you can tolerate! Also figure out sodium needs. Some are fine with the amount included in their gels/bars/etc, others (like me) need additional sodium.
-Time based goals are always hard for your first crack at a new distance, especially when you are new to Triathlon in general. Focus on consistent training and a full effort on race day and see where the chips fall. With a 1:40 open HM, you should be able to run a 1:46-1:48 HIM split, but it can be tough on your first go. I'm guessing you'll be a sub 30 min swimmer?
- Open Water Swimming: have you done much? any experience in a wetsuit? Boulder is later summer race so hopefully you will have time to get some open water swims in. Look for local tri or OWS clubs to join. Some "pool" swimmers find a wetsuit restrictive and you want to be very comfortable come race day.

Good luck and enjoy the process!

This is probably the biggest concern for me as I have never had to fuel during a race. Given a hypothetical 30 min swim, 2:45 bike, 1:45 run, how would you fuel on the bike? I would prefer to not stop along the bike route to pick up water/Gatorade but that might not be realistic. I'm planning on having a BTA and BTS bottle along with my bento box.

No experience here but I do have a few friends that live on lakes where I can get some practice. I'll be sure to practice with a wetsuit as well to get the hang of it.

You don't stop to get water/Gatorade. They hand it to you while you are riding.

Two bottles and a bento box should fit everything you need to start the ride with, save for one quick pick up of water from an aid station (and as noted, you don't stop, just slow down enough that you can grab the bottle from a volunteer)

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