The Off Season: My Trouble with Tracking Calories

In a day and age where the average person has a smart phone and lots of us have a smart watch or device, it is easy to get obsessed with tracking metrics like steps, calories and minutes of activity. I have been a huge fan of my vivoactive 3, and enjoy the data it collects all day and night.
I try to get lots of steps and stairs in at work, and I have derived some habits to get bigger numbers. For example, there is a staff bathroom directly below my office on the 1st floor. I'm on the 4th floor, so I always take the hike down and back up to use the potty. I can easily get 30 flights of stairs in between that and copies and delivering stuff around the building. When I add in the dog walk at night, I easily get 9 or 10,000 steps, which is really nothing. but it is a solid number. My average heart rate is usually mid 50's and resting heart rate is pretty low at 50.
However, these metrics are not super important to my health or well being compared to my diet. My blood work is a nightmare, and if I am not on my statin drug for high cholesterol, my cholesterol number is a good batting average. Yep, it is that high, a simple genetic flaw probably right up there with male pattern baldness and being short.
I know that simply watching my dietary cholesterol is not a big issue for me because my condition isn't so much caused as much by what I eat as it is by my genetics. Taking a look at what the RDA of cholesterol looks like is just scary. Tale a look at the info from Health Line, "What Does 100% of Your Daily Value of Cholesterol Look Like?" 22 pieces of bacon? Holy mackerel!
I am trying to follow the cholesterol lowering TLC diet which recommends less than 200 mg daily. I think I am in good shape, as I would almost never ingest anywhere close to that much cholesterol.
Exercising, losing weight, reducing fats and increasing fiber is a great way to lower those bad numbers. I have tried time and time again to track macros and calories. I have used My Fitness Pal and now Livestrong's Myplate, and each experience delivers the same result every time I use a diet tracker.
When I have a calorie or macro goal, I eat "towards" that goal. Sometimes, I do it even if I am not hungry. I could be perfectly satiated, and yet if I look at my calorie goal and it says I have 500 calories shy of my daily limit, and I have 78 g of carbs under my max... I might go eat some fruit. Or have a green shake. Or I might have a bagel. Yes, I am an idiot. An unstoppable idiot.
For me, the ideal tracking tool would give me the ability to track foods and macros but without telling me what remains. It would tell me how I am doing with the basic balance of macros (carbs to fat to protein). It would tell me when I am approaching a limit. So, maybe something that would pop up that says, "take it easy on the carbs for the rest of the day," or "your sodium is kind of high today."
Ideally, I could ask it questions. "Can I have a banana?" "How about a hotdog for dinner and some baked fries?" "Can I get cream in my coffee or should I stick with black coffee after lunch?" "I'm thinking of having a banana and a bowl of instant oatmeal for breakfast. What do you think?"
Those are the kinds of things I want a diet tracker to do. Right now, it is early afternoon, work is over, and I am trying to figure out how I am gonna spend the 1400 calories I have left. And I know I am likely to eat them all. Every last one of them. UGH!