I do gluten free a little different than some in that we have chosen to go in a more whole foods direction. That cuts way down on the label reading since I buy very little packaged food. We focus on fresh fruits and veggies, with some meat and "alternative" grains such as quinoa and amaranth. I also haven't gotten into a lot of the gluten free "replacement foods" such as breads, crackers, etc. but I do indulge in a store brand frozen pizza crust occasionally from Whole Foods Market. That has been the easiest way for me to approach the whole thing, but you have to find what best works for you. I keep a list of what we can eat on the fridge door. It helps if you can focus on what you can have as opposed to everything you can't. I do some gluten free baking. I have been slowly converting some of my favorite dessert recipes to gluten free, but it takes some time and trial and error. Some are easy like apple crisp -- I use quinoa flakes and gluten free baking flour for the topping. Some take a little experimenting. As for bread machines, I really don't know. I have an older one but haven't tried gf yet. We have pretty much given up bread instead of looking for gluten free alternatives. I did find this article that explains the bread machine requirements.
http://www.breadmachines.com/bread-machines/glutenfreearticle.cfm
We always carry our own snacks. Not having gluten free snacks is where we tend to get in trouble. For eating out we prefer salad bars and buffets, but some celiacs don't because of fear of cross contamination. We have also found good choices at grocery store deli's if all else fails. There are restaurants that have a list of gluten free menu items. Check restaurant websites or ask at the restaurant when you arrive, but don't count on your server to have this information. Here are a couple of websites that might help. Do a search on "gluten free restaurant menus" and you will find more.
http://www.glutenfreepassport.com/index.htm
http://www.alamoceliac.org/acddfastfood.html
Hopefully someone will jump in here who knows more about bread machines and help you out. The most important thing is not to panic -- this is all doable.