Ambie --
Thanks! I'm 5'5" and wearing size 12s (from 28/30s). Honestly, it's like a dream come true.
Yes, it really can be done! There are lots of calorie counting resources, including right here at 3fc
http://www.3fatchicks.com/food-calorie-counts/
Lots of people use online resources like fitday.com and the daily plate. Check them out!
I think a lot of times we get really hung up on the details. Calorie counting is great, but it's just a way of using portion control and keeping myself accountable. I weigh and measure things when I'm at home, and I do my best when I'm out. Lots of restaurants have some kind of items listed, but again, I do my best.
As for a reasonable amount, it really varies per person... how active you are, your metabolism, etc. Trial and error is often the way to go. Why not start at something like 1800 calories and see what happens for a few weeks? If you're losing 2 pounds a week, great! If not, tweak it. I lost more than 2 pounds/week for a while eating around 2000 calories/day. But everyone is different.
There's also a calorie counting forum here at 3fc. I read a lot there too!
Good luck!