For me, once I got into the habit of it, it's not a big hassle to do so. I think MFP is amazing, especailly considering it's free.
I'm not neurotic about it, I don't weight or measure things like spinach. I do weight most things though, cheese, jerky, salad dressing, meat, beans, etc.
I don't cook a lot. It's pretty pointless when I can only eat 2 oz. But when I do I use MFP recipe builder. It works really well, IMO. For a big recipe I just guesstimate on the number of servings.
I eat out a lot, and mostly at non chains. I also generally use the highest calorie option for a dish. I don't stress out too much over it, I figure logging, even if it is 100% accurate gives me a better record than not logging. MFP is fantastic about having ethnic dishes in their data base.