It's actually becoming progressively easier to be vegan from the practical standpoint. There are more and more vegan-friendly restaurant options, actual vegan restaurants, vegan quick food options in supermarkets, greater variety of protein-based products. In some parts of the U.S. it may not be the case, but at least on the East Coast (and especially here in Boston) and in the West Coast places I've been, it's not a problem. Also in Europe it's increasingly easier as well. Italy has the least options out of western European countries I've visited, but even there it's never a problem to find vegan food for the day or make your own sandwiches if you must eat on the go. A lot of Indian food is vegan, and it's delicious.
As far as cravings go, it's a mistake to think that vegan food is bland and that only a burger would satisfy. The problem is that there's lots of bland and boring, bad vegan food out there in places that just don't want to bother making it good or interesting, but again, it's becoming more commonplace to have super flavorful options that have lots of ingredients and interesting sauces/flavors. The food I eat at home is far from bland--I love very bright contrasting flavors. I honestly crave a good Sweet Green salad more than a bucket of chicken wings. Also, I used to be a complete cheese addict, eating those large blocks of extra sharp cheddar you can get at supermarkets at fast rate. Thought I'd NEVER give that up. Somehow though when I did, it's been absolutely not a problem. Every once in a while I think of non-vegan things I'd like and then other alternative things come to mind, and they are now equally enticing. Ice cream? Try some So Delicious cashew varieties--I see them in most US supermarkets now. Tastier than most milk-based ice creams in my opinion (also as a former ice-cream addict). etc.