Just a thought, but can you drive partway, park, and then ride the bike the rest of the way? Build up to the full distance while you build your confidence? All the planning and thinking in the world does not beat your personal experience from doing it

That is essentially what I did; started with a 2.5m (one way) trip, now doing 7 - 10 miles, each way, depending on how I feel.

Things I've changed, from the beginning, based on 'wisdom', based on 'experience', based on mistakes made:

-I don't rely on bungee cords to hold a jacket to a rear rack (lost jacket).
-I don't use an open, grocery-carrying style pannier to carry things (lost stuff)
-I do carry a packable rain coat.
-Spare tube, plus patch kit, which I (finally) trust that I can use, successfully.
-Know all the bike shops between car parking spot, and work.
-Have Plan B (and Plan C) in the event of major breakdown, or weather issue (haven't yet have to use).
-Triple check lights, brakes, tire pressure.
-Put all cycling stuff in panniers night before, put panniers where I will see then walking out the door.


...In other words, I've made plenty of mistakes, and learned from them. I used the forums as a leg up, but learned the most by doing things not perfectly, and then improving what I was doing.