My suggestion....pick up a copy of Veganomicon (see also the website from the author at http://www.theppk.com/ ). My suggestion is to aim for vegan and if you fall "off the wagon" you can fall to low fat dairy. Eating vegan is easy if you cook at home; if you dine out, vegan is harder to do than ovo-lacto.

As divingbiker said, start simple. Pick up some TVP and use it where you'd normally use ground meat. If you don't want to use TVP, bulgar wheat also works well. I make a chili where I fry up the onions, garlic, pepper, toss in the bulgar and spices, sautee until slightly toasty and then add the beans and tomato. Simple changes.

Disclaimer: I've been vegetarian for more than 20 years--I've yet to find a good vegan substitute for bleu cheese I come from a family of high cholesterol and, even as a vegetarian I've had my cholesterol too high. Oatmeal in the morning; red wine in the evening and consuming only a small amount of fat-free or low fat dairy has got me under control (well, except for that bleu cheese habit)

Good luck.