SwimFor the Olympic it's 2 anti-clockwise loops. The bay was fairly protected and very smooth and clear in 2017. It was cold last year (around 55 degrees from memory) but apparently this year it's 58 so should be fine with a normal cap on or perhaps a double cap. The start line is narrow but it didn't seem like people were too keen to line up near the front so it was a fairly polite start (see video 0:28). If you want to pick a side, pick the left side so you're not pushed wide around the buoys. There is some running on the sand between loops but it's just a few steps and not that complicated. Just a little annoying to get vertical in the middle of the swim.
T1There's a decent run to T1 but it's on a smooth path. They do make you do a "U" through the entire transition area to get to your bike which means there isn't a huge advantage in having your bike near the bike entrance as I normally recommend. Although, if you put your bike shoes on in transition, which you shouldn't be, you probably want your bike close to the bike exit so you're not clacking around in your cleats. There's an argument I suppose to have your bike close to the entrance of transition from the swim because although you're forced to push your bike through T1 longer you'll have more time in your running shoes getting out of T2. I'll leave it up to you, folks.
BikeIn 2017 there was headwind but not ferocious and probably blowing a bit more in 2018. The point is you're probably going to be faster on the return so don't freak out if you're not on your average goal pace on the way out as you might be able to get back on track on the return. You have to go by feel. There's one 5% grade at 6 miles but that's the only time you're out of aero. The rest is undulating. All and all an interesting course. I did hear some people got stopped on the way back into town by a light but I must've struck it lucky because I was never impeded. The table below shows distance, time and average speed of the 1st half to the turn around and second half on the way back. As you can see that's a 3.5mi/hr differential between out and back.
As mentioned you come in the same way as you came in for the swim and have to run around the entire "U" transition area again. A little painful on the footsies but they are likely still frozen anyways.
I had been injured last year and not particularly fit but even if I had been the run was BRUTAL. There are some normal sections on the way out, on some sandy trail and suburban roads. You won't regret holding back here because before the turn around you hit some hill and stairs and then on the way back it is ALL in the sand. Some sections (like 1:50 on the video) you're forced onto soft sand. The majority of the way back, about 2.5 miles, you have the choice between quick sand, near the water edge, or pure dry soft sand. I couldn't tell you which was the worse option. Either way you're going to be running at least about 1min/mi slower on the way back if the sand was like it was last year. So factor that in as you're running to the turn around and make sure you've saved plenty of energy for the return. Oh, and don't take your shoes off. I don't think anyone was disqualified but it's actually illegal so you could be. The finishing straight is paved and feels like heaven.