Started at 283. Down about 45lbs over 3 years through diet, biking, and buying a 10 acre plot.
I'm noticing that as I lost the initial ~30lbs, it's getting tougher to actually lose weight. I'm losing SIZE, but not weight. I'm down 2 belt notches since January but only 3-5lbs depending when I weigh in.
I've noticed that my (well meaning but generally idiotic) coworkers treating me differently. Random comments about being a "big guy" are much less frequent.
Clothes are cheaper. The brand of khakis I wear to work would charge $15 extra for the combination of loose fit + extra rise that I needed house my thunder thighs. So not only am I down in the waist, I fit an off the shelf size again, saving me $75 a year, give or take.
Probably most importantly, I can now tell the difference between how I feel when I eat like crap and when I eat well, in terms of both quantity and quality.