Shmead, all your tips are awesome. I like the idea about looking up what you will eat and logging it before you go to a restaurant - being in my 20s and just out of school, I tend to meet up with friends on the weekends a lot, and that's usually the thing that knocks me off plan. I like your idea better
I love Lose It! In particular I like that you can get to your log from your phone or through your web browser, and the other updates automatically (if you use it both on your phone and online), and I also like that you can create your own recipes and custom foods that will stay in your list of foods forever, so you only have to calculate all the ingredients once. Highly recommended.
As for dealing with logging calories... having a good tool helps a lot, and I also eat the same things frequently, so it's easy to just copy previous meals over to today and then not worry about it. I too like to log what I *know* I will be eating as early in the day as I can remember, and then I also have an idea of how many calories I have left over for the day to work with - e.g. if I get hungry in the afternoon I know I have X calories to use apart from breakfast, lunch, and dinner, and that helps me make an informed choice of afternoon snack.
Good luck katy trail - the hardest part is starting, of course, but you've done that now, so the rest is easier!