My handwriting has always been terrible. It was a big issue in school until I was able to turn in printed assignments.
Like with a lot of school things, they do a shit thing without thinking about negative effects. They always want a simple solution to a complex problem.
I've always tried to estimate more time than I think a task will take unless I know it's only like a simple task.
If I think it will take a few hours, I estimate a day. A day or so is 3. 3 or more becomes a week.
I've ran into way to many tasks somone else blindly put at a day and when we start to work the ticket we descover a ton of complications. I've seen so many 1-3 point tickets I've seen take multiple weeks because nobody thought about how deep the rabbit hole could go.