I toured in the winter in Canada and I didn't find it at all that bad, but I was able to stay indoors almost every night. You should definitely check out warmshowers.org, if you haven't already. Also there was a thread about winter touring last year, not what you will face, but it may be helpful. Winter Touring Help

Definitely do some test runs in the spring, when the weather would be somewhat similar to October. 1-2 day loaded tour would be great too.

As for enjoyment, its really just about how you look at it. But as gif4445 said, if you don't enjoy it you can always pull the plug, there is no need putting yourself through something you hate just for completing it.