My only stolen bike in my adult life was when I stupidly used a cable lock downtown. Luckily it was a Huffy, but unluckily it was only 2 weeks old. I bought it, a helmet, and the lock for $150 to see if I would really start commuting, but still, only 2 weeks old! Sure, it wasn't a 'good' bike, but for a Huffy I was impressed.
Anyway, since I've had my Fuji's (first an Absolute, then a Royale) I've been lucky. I lock with the sheldon brown method, a fat cable for the front tire and a Bulldog on the rear wheel. Everything is quick release, and it comes with me. Lights, fenders, pump, etc. Just pop it all off and stick it in my seatbag and then carry the bag around. If I'm just cruising around town I'll leave most stuff at home, just take the lights and pocket them when I stop somewhere. And when I stop, the bike gets locked, no question. Even if it's just for a minute. I'll spend 5 mins locking/unlocking the bike and 30 seconds in a store, I don't care. I carry the lock everywhere too. 3lbs doesn't matter - I weigh 190lbs with a 20lb bike, so it's like 1.5% of my weight. It makes no difference, I'm not running the Tour de France.
I would never lock it outside overnight though - that's just craziness. Even in the good neighborhoods there are spoiled 15 year olds who'll jack stuff for fun. I get rides or grab a bus to get the bike if I *really* have to leave it for some reason

I've left it locked in my office garage overnight, but they have huge bolted-in-cement crank-case locks with a massive chain plus my bulldog and cable, the gates close at 6pm, and there's a guard.
--Illah