u/Efficient-Finish-496

So I've never dyed my hair before, always wanted to but when I lived with my parents they wouldn't let me then when I got into a relationship he also asked me not to. I'm now single and old enough to do what I want and I really want to dye my hair dark, like either very dark brown or black. My hair is mousy blonde and gets greasy really quick but otherwise in good condition. Those of you who colour your hair regularly, do you wish you never did? Do you enjoy the upkeep or find it tedious? Is it an expensive habit even if I use box dye? I feel like because I've never done it before, I should just stick to my natural colour, but I really want to change my appearance