Over-explaining is my biggest issue. I’m entirely self taught and the trash quality of certain softwares with non-descriptive variable and function names sort of steered me towards clearly naming things (sometimes verbosely). That has the unfortunate side effect of repetition when documenting and it comes across as sarcastic or condescending when proofreading.
Its far easier to have a machine do it than to second-guess every sentence.
You mentioned a llamafile, is that offline? I’m using GPT-4 at the moment because my partner has a subscription. If so, I maaaay have to check it out ^^
Have you looked at Duplicati? I use it and find it dead simple and reliable (I did a full recovery from a total data loss last year).