Originally Posted by
BobbyG
Don't over think it, just do it.
^ This.
It's easy enough to get into doing a trip. And then, once you've figured out the basics (a decent jacket, the right spare clothing for the destination, how to clean yourself before dressing at the destination, lighting, etc), the rest will come.
Might try a few long-ish rides (at "commute" distances) several times, until you're satisfied that "the basics" have been covered. Ensure you're lighting's up to snuff. Ensure you've got decent rain-proof gear that'll get you to the destination without feeling like a drowned rat. Ensure you've got enough basic fix-it tools and spares to cure the obvious likely issue of a flat. At which point, actually commuting makes sense. The rest will come, eventually, as you work out what's really necessary, what you've forgotten. But in the meantime you'll be racking up those miles, gaining the benefits of fitness and well-being. As others have suggested, by the end of a year of doing it nearly daily you'll find most of the kinks worked out, your gear a useful, capable combination, and I think you'll find you're doing it quicker and with far less drama and stress than you ever thought possible. It'll have become your thing, your way, and you'll be "in the groove." It's cool how relaxing and stress-free such travels can be, once there are no more "kinks" in the journey.
Hopefully, you'll be able to select from two or three possible routes in order to minimize your time along sketchy sections of roadway. Be sure to have great and visible lighting, good reflective tape/gear, etc. I used to commute ~7mi between two towns, the two road options between them being a no-shoulder two-lane country road and the other being a 65mph highway that had a good ~7ft of "emergency/shoulder" space off to the side. Never did like it, but got used to it. Turns out, the highway was safer, even with the speeds; that country road could cause perma-pucker, I kid you not. Since then, they've redesigned the country road a bit, so it's vastly safer for cyclists than it used to be 30yrs ago.
Good luck with the rides. Think "Nike" (as in: just do it).
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