I've been grinding my own wheat and developing my dough by hand for a while now. Here's what I use:

• Grinding: I use a WonderMill and have been very happy. Others have had good luck with a NutriMill. Both are what are known as impact or micronizer grinders. The advantage is that they grind quickly and require very little cleanup or maintenance. But, alas, you can only get fine flour out of them. Some folks believe that the flour one gets is inferior because there's too much starch damage. Personally, I've not been displeased, but opinions differ.
• Sourcing grains: I get my grains in 50 lb bags from my local foods co-op. If you've got a natural foods store or a health food store nearby, they can almost certainly special order bags for you. I store them in 5 gallon buckets outfitted with a gamma seal. The grains will keep for years.
• Hand developing dough: I rarely hand knead my bread any more. Instead I use the stretch and fold technique or the French Fold. Most of my breads involve a pretty long fermentation, so these techniques work well. Here's the bread I make most often these days: Whole Grain Hearth Bread.

My suggestion is to invest in a copy of Jeffrey Hamelman's book BREAD, A Bakers Book of Techniques and Recipes (or any other of the excellent books available).  Take advantage of the videos available on this and other sites showing various techniques; mixing, shaping, etc.  I personally think Hamelman's book is one of the best for a someone new to baking.  Read and re-read the 11 steps (pages 4-24).  Understanding these steps is key and will help you immensely as well as save you time and frustration as you move forward in this sometimes rather complex process.  Hamelman's book will provide answers to most, if not all of the questions you posed. 

 HO

You are at the right place in more ways than one.  Montana grows great wheat. I've been using the 'Wheat Montana' brand of flour and really like it (a friend lives there and brings me bags of it.) They sell the wheat berries too, see their web site. Also, you're at a good website here -- TFL has many answers and even more ideas than you'll ever think of. I've learned a lot from just reading.

I recently purchased the Hamelman bread book and agree with holds99 that it has tremendous merit, though it takes a while to get the gist of his recipes. Start out with other library bread books plus Hamelman's and you'll have a good foundation. 

Here's my thoughts for what they may be worth.

• Grain and Milling:  I have a Diamant hand turned grinder. As you may have learned on these pages, I have a somewhat unhealthy love of it and its versatility, quietness, and beauty.  There are less expensive hand grinders such as the Country Living grinder that might be fun if you want to hand grind and want to be able to produce cracked wheat, separate out bran, and do specialty flours.  As for grains - you are in prime wheat country - you should be able to find excellent local sources.  I buy from Bob's Red Mill - they are a reliable source for me. there is a site http://waltonfeed.com that has an excellent comparison of various grain mills.
• Equipment: I seldom use electric equipment.  I mostly develop my doughs by hand, using a technique described in the book "Bread: A Bakers's Book..." under the recipe "Unkneaded Six-fold French Bread"  However, for some doughs (especially breads containing milk and butter), I use a hand turned bread bucket, or in very rare cases my Kitchen Aid mixer.  But , let me suggest that you can use the "dough" setting of your bread machine. You can use any recipe that will fit. Some types of bread will work better than others, but you can experiment.
• Books: I agree with the posters above. After decades of baking bread (and good bread, mind you) his was the first text to really speak to me.  If you buy it (and I am told that there are better books for beginning bakers, although having been an experienced baker all of my adult life, I cannot help you with this) be sure to really read it - not just the recipes, but his notes and stories. It will inspire you. You will find that he is writing in terms used by professional bakers, but there is nothing in his book that you can't simulate at home.  That being said, decide what bread you want to bake.  Do you want to bake the sandwich loaves that mom used to make?  Do you want classic, crusty baguettes (mom probably didn't make those)?  Do you want hearty, European rye?  Define your goals and you will know where to focus your efforts.  Frankly, I learned to bake pan loaves from Betty Crocker and after years of studying "artisan" techniques, for good loaves of sandwich bread there is nothing wrong with that approach.
• Community:  The good people on this site are always ready to offer help with baking failures and congratulations on baking success.  It is an amazing community.

Hope this is useful to you.

Happy baking!

Pat