If you are going to do any serious off roading in the woods, make a set of Brake Snakes.
The first time you snag a bush and the shifter/brake stays where it should be it'll be worth it. Use good quality stainless cable and those aluminum cable ferrules so they won't rust, make sure to crimp them TIGHT! and a little vinyl tubing slid over them makes them look nice.
About the boots: even though they make it tough to 'feel', don't ride without them! A set of Alpine Stars saved a good friend's right foot when he nailed a chunk of granite hidden in tall weeds and I'm sure they have kept me able to still perambulate as well. About shifting: it's not necessary to get the whole toe under the tip of the lever in order to upshift. With some practice, you'll be able to use the edge of the sole which makes it much easier.