I'm guessing you're in the public system? Isn't it annoying when you see a different doctor every time and each one tells you something different. I expect to do the Dr shuffle in a public hospital, but within the one clinic you'd think they would have a consensus on treatment!
Sorry to hear you are feeling down with all of this, I do know exactly what you mean though. I equate the finger *****ing with getting on the scales each morning and having that determine whether you're in a good mood that day, or a not so good mood. Except instead of doing it just once a day, you have to do it four times. It sucks!
I haven't given myself a day off, but I did give myself a meal off a couple of times. My birthday was one such occasion, I felt it was fair enough. On the topic of chocolate, I have found I can eat a bit, I just have to make sure it is only a small bit. I've found the chocolate they sell at Aldi a godsend. It's called Moser Roth, and comes in different varieties. The best thing about it is you buy a block, but it's made up of 5 individually wrapped portions of about 25 grams each. So not a lot of chocolate, it doesn't get my blood sugar up if I eat just one, and it eases my chocolate cravings. If you stick with dark chocolate (the mint choc one is beautiful) then all the better because dark chocolate is low GI. Maybe try one of those and test your levels after that. If they are ok you could work it into your daily rations!