Yah, agreed. Half marathons seem like a good distance. Challenging, but no special training is required once you get into decent running shape; it's basically just your weekend long run, plus or minus a mile or two.Yeah it's a bit of a drag, but worth the marathon experience. It's the only time I get strict with a training plan is when I run a marathon, I need some kind of planning structure. I want to do well and be prepared, nothing worse than being under-trained for a marathon. This most likely is my last marathon for a long time, or forever. Between family, kids, work the training takes a toll, at least for me it does.
I love half marathons, just a perfect distance! I pretty much stay in half marathon shape all year around, much easier to do than a marathon, plus you can sign up for one at the last minute and feel ready for it. I have about 4 lined up for 2014 already. As far as the winter challenge it's there for the fun of it.
Still not sure about races in general though. I mostly like heading out alone with no pressure to run particularly fast. Some days I feel it, and push the pace, other days I just coast. It would suck to have to run fast on one of those days when you feel like coasting.
Like you, I flirt with a purely 'just run' approach from time to time, but often find myself retreating to a more numerological stance. It'd be nice to get the numbers out of my head once and for all, to the point where I could just head out without even knowing what my route distance would be. That's the way I used to run.
I know the Winter Challenge is just for kicks and giggles, but if I were to sign up, then it'd influence route choices, time of day I run, and I'd have to keep track of when I put on back-up shoes on those runs where conditions turn out to be less favorable that they seemed initially. This coming winter, in borderline conditions, I also want to experiment with running the first mile or so shod, until the running metabolism kicks in, and then go bare for however long I can. If I were participating in the Winter Challenge, I would probably want to start out bare right from the start. Basically, I need to protect myself from my own OCD tendencies.