I’ve been vegan for about 4 years and vegetarian for about 12. Giving up cheese was definitely the hardest for me. Everything else has decent substitutes, but vegan cheese is sort of its own class of food. It tastes good, but not really like dairy cheese. My method was to cut out cheese completely for at least a few months, and then try the vegan cheeses again. So, for any foods you REALLY love that aren’t vegan, I suggest not having it at all so you aren’t constantly comparing the vegan version to the real thing, then once you can’t really remember what it tastes like, get the vegan version.
I saw in one of your replies that you’re in Portland, so I doubt you’ll have any problems at restaurants. HappyCow is a great site for looking up restaurants in your area.
For cookbooks, I recommend: Veganomicon, Appetite for Reduction, Hearty Vegan Meals for Monster Appetites, 30-Minute Vegan, all of Isa Moskowitz’s dessert cookbooks (my omnivorous family has loved everything I’ve made from them), and Fresh from the Vegan Slow Cooker. There are also tons of blogs with great recipes, so search around online.
You also mentioned your main reason is for the animals (mine is, too), so something that helped me whenever I had a craving was thinking, “It tastes good, but am I willing to kill for it?” The answer was always no.
PLEASE DO NOT TAKE IRON SUPPLEMENTS ON YOUR OWN! Iron can be deadly if you take too much, and iron supplements should NEVER be taken without first doing blood tests and working with a doctor/nutritionist to find the correct dosage. I’ve never had iron levels below the normal range, and it’s actually better for you to be on the low end of normal than the high end of normal. Do take B12, though. It’s water soluble, so you pee out any extra.
If you do want medical expertise in making the switch, I really suggest a nutritionist over a doctor. Most doctors receive only a few hours of training on nutrition and aren’t really equipped to properly assess your diet.
Feel free to PM me if you have any questions? I’m a total foodie and love talking about veganism.