The wheelchair isn't a good idea. It's not paved and there are a few tree bridges which aren't going to be wide enough right off the bat. You might be able to see a little bit (.25 mile) before the first big bridge if you don't mind carrying a wheelchair over a small wet patch.
I don't think so unless we have a couple of days where it's dry and not rainy.
Thanks! Your answer is awaiting moderation.