I exercise daily, but this watch helps me push even more. I never really know how much calories I burn, and I don't know how accurate the Apple Watch measures, but as long as it is consistent, I'll be pushing my goal of at least 700 calories a day. I'll adjust it over time.
Same boat. Like OP, for years I tried (sometimes successfully) to lose weight. Around 18 months ago (turning 40 had a lot to do with it) I basically begged a buddy of mine to take me on as a project in the gym. He was game and we started to workout together 2-3 times per week. Since then I've lost 30 lbs and gained an actual shape. It's nice.
So, how does the apple watch fit in? Even though I'm already motivated and in the habit of regular exercise, the Watch motivates me that much more. I'm far more conscious of how long I exercise each day, I try not to sit much, and I MUST complete the rings if at all possible, even if it means a midday or evening walk or extra rowing / biking session. I can already see results on top of my previous improvements. It's really a great device.
Good luck to everyone trying to get in shape... stick with it and use the watch to help motivate you. Anyone can do it... even if you've tried 853 times before