How can I make calorie counting less painful?

I'm not a fan of calorie counting. I've never been a numbers person, and in addition, my black-and-white thinking causes me to go to some extremes when it comes to counting calories.

At the same time, while I did lose a few pounds eating mostly real foods, I'm aware that I may not get very far with this since my diet isn't 100% perfect. I may have to count calories in the future.

I'm just struggling with how to do it without losing my mind. Because I'm doing a lot more cooking, everything I eat requires accurate measurements. Even if I have roasted sweet potatoes with olive oil and rosemary, the amount of potato will have to be measured each time, so I can't just add that dish from my favorites and be done.

Take an apple. I usually slice and serve, but sometimes, I do eat it whole. I've always only weighed the portion I've eaten (I weigh the slices). If I eat it whole, I'm weighing the core too. Do I eat it and put the core on the scale to figure out how much I actually ate? What about pears? Fruit with pits/seeds? Should I weigh my cherries before eating, and the stems/pits afterwards? Do I weigh an orange before or after peeling?

Same with chicken. I prefer drumsticks and such over boneless breast meat. Should I weigh my chicken before, and bones after? Should I weigh my pistachios in shell, and then weigh the shells afterwards? When I eat at home, it isn't too big of a deal, but it's different packing a lunch. Those scrap/waste pieces can dry up between lunchtime and getting home to put it on a scale.

I don't plan on doing much with my tracking to start. If I decide to start really tracking, I'm just going to start measuring what I already was going to eat to build awareness- not to try to stay in a certain calorie range. I'll see where I need to go from there.

But even the idea of counting calories with no pressure or restrictions (aside from my usual avoiding junk/processed food 80-90% of the time or more) worries me.

Any tips? It seems like this was a lot easier my first time on Weight Watchers. Not because of the WW program itself, but because I ate Lean Cuisines, Smart Ones, and dinners at Subway, Cosi, Panera, and the Applebee's WW menu frequently. I lived primarily off of prepackaged/processed foods. Now, even my prepackaged foods are whole grain microwave pouches, organic whole grain macaroni and cheese (Annie's), frozen seafood/veggies/fruit, and all-natural/uncured meats- including hot dogs for the mac and cheese).