Sure, I’ll give an overview, there’s a lot more reasoning than this, but it should give you an overview.
Why Calendar: We want users to be able to plan their training. It’s as simple as that. It also opens us up to do a bunch of cool things in the future.
Why web first: We think that it’s easier to manage a calendar with a keyboard/mouse than with a touch screen. It’s also easier to build for the web than for apps. Because of this we went web first, then apps. The clunkiness you feel will be improved. We still think it’s a better experience than our previous experience.
Why not “Bingo Card” training plans: There are some people who want us to do it how we used to have it, where rides were on Tuesday/Thursday/Sat and they could do them in any order and they just did them one at a time.
I hear you on this, and I think you’ll be happier with what we have coming. I also think you’ll like it like 100x more than the old way.
tldr: Calendar is for people who want to plan their training. If you don’t wan to plan any training, I can see how it seems useless (because it is). We have features coming out for those who don’t want to plan their training.