I don't really have to help her with tech, however, let me just brag a little..
I convinced my mom to try out Linux a few years back. To this day she still uses Manjaro, and tells me she has less issues than in her Windows days. So proud.

Worst busywork?
Having a graphic designer on the team that doesn't know development.

Gods, the amount of tweaks and adjustments they come up with.

My gods, fuck WordPress in the backend!
Why did my company decide on writing a data collection api with many dynamic pages on top of WordPress. It's a blog, not a wonder tool you dumbwits.
Never have I had more fuck this moments per hour..

So my local job center had me convert my LaTeX CV into Word format, as apparently PDF is to techy for them.

Worst experience was being kicked out of university. Best thing was the job I landed right after.

My favorite dev tool has to be make. Imagine having to build and link everything by hand! *shivers*

"We're migrating to apple"