How many decades to you want to be dieting?

Yesterday, I met a woman in her late sixties who was giving a lecture on how to use various office software. I figured I'd pick her brain on course structure for multi-level students since she has been doing training for years and I've been working on FOODBOSS™.
But we didn't really get to the part about course structure because she wound up revealing to me her long term "battle" (in her words) with yoyo dieting. She has had her thyroid removed, has diabetes, and has been calorie counting and tracking what she eats every day.
She even told me that she has been tracking for 512 days in a row(!) without missing a day, and that she travels with a scale to weigh herself and another food scale to weigh produce she buys.
I was intrigued. My questions for you are:
Do you want to train yourself to be an expert in tracking, counting, measuring, and worrying about your weight for the next decades until you are her age (and beyond)?
Do you want to go about every day of your life thinking that you are either "on" or "off" the "bandwagon"?
Or, would you rather train yourself to actually find what you and your body like so that tracking and counting and measuring don't come into the equation (wait, equation? why is eating a math problem!?)
If there is one thing that I find common in yoyo dieters, it's that we tend to be scared of food. 
It doesn't matter if you identify yourself as someone who has a lot of diet knowledge or someone who isoverwhelmed with diet information - we all sit in the same boat of either being genuinely scared, or second guessing what we eat.
But you know what? Yo' Mama (aka Mother Nature), she don't want u fat, yo'. She wants you to be naturally glowing and feminine so you can attract all those male dudes and make babies and frolic in flower gardens. So that's why she gives you all these beauty products (natural foods). These are the foods you don't have to be scared of.
There was one thing that jumped out at me over the course of the conversation:
She was very knowledgeable about calories and protein and carbs and sugar and anything to do with tracking. But she doesn't focus at all on food quality. Getting mayonnaise pasta from a convenient store or having a fresh piece of fish in a restaurant made no difference to her as long as it was within her calorie range.
, eating a 200 calorie chemically processed chocolate bar that you got in a vending machine is not the same as eating a 200 calorie organic raw food chocolate bar. They look the same and taste the same,but the effect that each will have on your body are completely different in terms of your weight, your skin, your hair, your energy, your digestion, and your well-being. So yeah, pretty much everything. So, why not satisfy yourself with the one that makes you look gorgeous?
Hey, you don't have to listen to Yo' Mama. You're a grown up, after all. But you do know in the back of your head that Yo' Mama's always right. And you have to trust that if you eat what she offers, you won't have to worry about your weight!