Have you considered something with drop bars? That would help some with headwinds. I doubt you can get very tucked down on the sidewinder.

Is the shoulder you ride on paved? Gravel grinding definitely needs different tires than a paved shoulder.

Do you anticipate becoming a lot stronger rider than you are now? If you struggle some now with 38x16 then multiple gears are probably a good idea. I doubt your current gearing is too much fun when you have a killer tail wind that you could be taking advantage of.

Do you want to do anything else with the bike other than commute?