Four Recommendations

I'm still working on the huge entry that will appear below this entry, but wanted to write a quicker note. If you only try four gluten-free products, these are what I recommend:

Tinkyada pasta. A lifesaver, especially if your family eats a lot of pasta. You can simply cook two pots (one wheat, one Tinkyada) and make the same sauce for everyone.
An all-purpose mix--Pamela's or Bob's Red Mill. They have recipes on the back and can be used for muffins, pancakes, waffles, bread, and I think even cookies. Baking from scratch can be very daunting, especially if you have to buy all the flours, so a mix is a perfect way to get baking.
Rice Chex, Corn Chex. Gluten-free cereal that is easy to find and cheaper.
MiDel Gluten-free cookies. Because everyone should get to open a bag and eat a cookie sometimes.

Places of Note:
Whole Foods. If there is a Whole Foods near you and they have a gluten-free bakehouse, it is worth splurging on any of their products. This is not something we do very often due to the price, but their cookies and muffins are so good. Try this if you're feeling discouraged about gluten-freedom.
Wild Oats. They also have some tasty chocolate chip cookies, if they still do. I have been away from Wild Oats for nearly two years, but they have had some tasty options in the past.