I have been maintaining my weight for a few years now, and still, every single day I weigh all of my food and enter it into the Nutrition Tracker. My motivation is that I am NOT going to be gaining weight again. I was overweight most of my life, and for me it was a very fine line between a calorie range that worked for me, and one that didn't. I was gaining on an average of 1650-1850 calories per day (from a very healthy diet), and most of the time I was gaining, I was doing quite physical work on a daily basis. I keep a spreadsheet and after my metabolism had had it's butt kicked, I discovered I could maintain on 1600 calories average - above that and the weight slowly crept up - below that and I slowly lost.
As I said, it is a fine line and one that I am not going to cross again!
I think that most people do relax their tracking after a point. The key is knowing what you can let slide (lettuce and a lot of vegetables for example) and what you really do need to pay attention to (fats, slices of cake and cookies). Slower losses due to relaxed tracking also are a state a little easier to maintain than constant vigilance over everything. Some people do really need to track everything forever, and that is okay, but do play around with what level works best for you. Slow and steady allows you to make changes that are easier to keep long term, even if that means slower losses in the short term. That's actually not a bad thing.
One thing that you may want to do is to play around with the numbers and see where you maintain now and where you would maintain at your goal weight. Look at those numbers along with your loss range numbers and play around with them. If your maintenance range now is 600 calories higher than your loss range it is okay to sometimes eat between the two ranges. Slower losses than your loss range, but at to under maintenance is an okay place to be. There are some people that eat at their goal weight maintenance ranges, which tend to be under maintenance and above loss ranges, but it gives them a lot of practice at eating where they want to be ending up. Towards the end of their losses they usually end up eating just under their goal maintenance, but they get a lot of practice doing what they want to do long term in the short term.
You also have to get really good at looking at the forest and the trees at the same time. Losing weight the fastest and losing weight and keeping it off are not the same goal. What is what you want and how does what you choose each day contribute to your long term goals?
I've gotten myself into a groove with healthy living for the most part. I haven't fallen off the wagon in a while. But I do find myself getting not as strict about measuring my food and choosing healthier foods even when staying in my calorie zone. I know I'll have more success if I pay attention to the little details. How do you motivate yourselves to keep being vigilant long term?