Transfering data from your PC to your PSP now isn´t difficult. There are many programs to make it easy, like this PSP Max Media Manager 1.32 which is a transfer manager that´s completely free. It lets you transfer files from one to the other (music, videos, matches played, etc).
To do it, you don´t need IT knowledge, just connect the PSP to the PC and then choose the files you want to transfer. There are two ways of working depending on the files you want to transfer.
If it is music or images, PSP Max Media Manager 1.32 makes an exact copy. If you want to transfer video, what it does is convert the file to MP4, which, as you know, is the operating format for a PSP. For images it is especially useful, because in addition to transferring them it classifies them by size.
Obviously this program needs you to have a PSP.