Painting over a repaint

It’s going to come down to what your mental idea of “not perfect” is before you start the job and what you actually see once the project is painted as being “not perfect”. If the two are the same then you won’t have any issues. However, if they are different, every time you look at the truck once it’s done, you will say to yourself “I should have taken more the old paint off first, I should have filled the dents more, I should have removed all the trim……”