I'd start by making a list of everything you like. Then plan from that. That's how I started, but now it's morphed into me stocking up when things go on sale and planning from what I have in the house. I think I started planning a week at a time and now do a month. Plan for leftovers. Like if you make a roast, have sandwiches with the leftover meat the next night (or whatever). Shop in season and shop sales and you'll save alot of money. And when you're completely stocked, dinner will be much easier, even if you don't plan.
I freeze in plastic. I know it's not that popular, but glass scares me. There's a huge thread here about freezer meals, but I stick with breads (bought really cheap on sale), meat and whatever produce I can get my hands on during the summer. We've still got a couple bags of fruit and some veggies from last summer.