Crosstailwinds really amplify aero wheel effects, esp with a taller wheel.

I rode in Hurricane George (Coconut Grove area to the Key Biscayne causeway and back) on dual TriSpokes with two other riders. It wasn't pleasant but we didn't take each other out (and trust me, I was drafting as close as I could). On the way back I went 60 mph for about a mile. It was a blast and worth every moment of suffering elsewhere.

Head on you'll see that wheels don't differ much - it's the crosswinds that make the difference.

If you do mainly TTs, I'd build a repertoire of wheels, going taller and taller until the wheel you get last is unmanageable in all but the calmest days.

I'd also get bigger gears. I know that that technically it's possible to go really fast on smaller gears, but that high cadence (120 rpm or more) comes with a price. If you have bigger gears that you can turn slower, you'll reduce your heart rate a bit. Not important for hummingbird types, but for me it's critical. When I move up hard or am sitting on a fast moving line of riders, I'll purposely gear up to reduce cadence. So get an 11T at a minimum for the front (no 12s or 13s). Up front a 53 minimum, maybe a 54 or 55, even a 56.

A plus: even if you don't use a 56x11, the jump between the 14 and 15 is smaller when using a 56T ring. This is because a one tooth difference is percentage-wise lower on a 56 versus, say, a 50.

Along those lines I'd also use a bigger inner ring. If you can go really big I'd do a half-step set up, where the two rings are so close that the inner ring is a half gear down from the jumps on the outer ring. Usually this requires a 4T-5T diff (48/52). A 48x12 is between a 52x12 and 52x13.

You can also figure out the biggest gear you may use going out and get a ring that matches that gear with your 11T. Maybe it's a 46x11 for example. Make sure your low gear allows you to get up the hill okay (46x23?). Then you don't have to keep shifting the front derailleur - you shift it once, at the turn around, and then you use the outer ring on the way back.