I bought myself a food weight to have at the kitchen but just like you I struggled with all the minor things that gets added in rapid succession. The trick is to get good enough at estimating within reason, and focus on one aspect such as calories.

Figure out what one table spoon of oil contains, and when you make a sauce use a table spoon while pouring to count roughly how much oil you are putting in.

For shared meals, or self-restricted portions, I just add the entire meal upfront to my book-keeping, and then after are are done eating I subtract what I didn't eat.

You don't need to keep track of the family history of your cucumbers.