I asked something similar.
It does feel overwhelming! My b-day is coming up and I'm hoping to get a food scale, and eventually hoping I'll be able to eyeball portions better. I'm a bit worried I might become overly obsessive and start weighing everything though.
I liked the idea of just rounding off if I can't find the exact number of calories...counting an apple as 100 and not worrying over if it's small or large or how many oz. it is. As the poster who said that pointed out, we didn't gain weight from eating a little more or less of an apple (or lettuce, vegetables, fruits...)
When I have a better idea of about how many calories are in foods I eat the most often it'll probably be quicker to just jot down in a pad. Planning on the free sites is helpful to give you an idea what to eat but sometimes things come up that you didn't plan or you might not always be around a computer.