I thinking planning how you use cheese in advance is a good idea. I have found that cheese can stall me, so I tend to err on the side of caution and use it sparingly. If it is dinner, and I haven't had much for cheese, I might put it on a hamburger for example. But if I snacked on cheese earlier in the day, I won't.
A couple of the cheese brands I use have bags of individually wrapped cheddar cheese pieces. Each are 1 oz. I find that helpful to track how much I use. I know I use enough heavy cream in my coffee that I don't have much allowance left to use it for other things. So yes, I count and measure.
As for jello, if you can find Hunt's jello cups...they make a sf version that is made with sucralose. Double check it, but that is what I use (though again, I use it sparingly).