Disclosure: I didn't take the time to read the thread, but here's my thinking.
I buy meat in bulk and cut it up in just over 1lb portions to make up for lost weight after cooked, and freeze it. So, when I cook dinner I cook the lb and it is pretty easy to tell if you're eating 8oz, slightly less, or slightly more.
For bulk tupperware food it really depends on my goals and the food I'm eating. So if my goal is to get down as much food as possible I never weigh my chicken salad because I eat an insane amount of it, but for cutting when I'm still trying to keep my protein high and I have a giant tupperware full of cold chicken breasts I have to weigh it because plain dry cold chicken breasts are one of the hardest things for me to get down.
On the other hand if I'm running ghrp6 before every meal then I don't worry so much about it because I know I'll put food down like a craved lunatic.
Basically, for me, it's all about the particular food and my current goals, but as far as extra lean meat is concerned I don't usually take the time if I know I'm going to eat more than my portion because I don't really care so long as I eat at least my 8oz. But for red meat I do usually watch my intake a little more closely.
EDIT: This isn't going to be for everyone, but it's my system and it works for me.