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The only negative point i have with that option is that those save files are unusable as they are on your computer since they are stocked as. It also doesn't care if those save files are copy protected or not, it let you copy them on your USB Drive anyway so save files from games like Monster Hunter or Timesplitters: Future Perfect are no trouble at all to move around. I transfer those save files with the help of an European action replay called the "Action Replay Max-2", that AR have an option called Memory Max that can let you transfer your save files from your Memory Card to a USB Drive and vice versa (it can only detect a small USB drive, small in data size i mean, i don't know the limit of the size it can detect but the one i use is 125 MB) and once they are on your USB drive you can easily transfer them to your computer, the memory card shown on my first picture below called Max Memory is not really mandatory since you can use any PS2 memory card with it but i put that as an HUGE WARNING: that Memory Max option can not only corrupt your save files but can also corrupt your entire Memory Card, it's apparently pretty rare but it can happen, but in almost 10 years of use i never had any trouble with that Memory Max Memory Card, even though i tend to stay safe by copying the save files i can copy to another memory card before doing the transfer (that option can also format Memory Card so it can really be helpful if you stumble across a corrupt one during your hunts like i've found two of them a few years ago).
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I never used nor even own an HDD for PS2 before so i can't really help on that side but i transfer my Playstation 2 save files to my computer for almost 10 years now, and it did really help since i have so many games on that console, it was pretty mandatory for me to do so unless i wanted to delete thousand of hours of play.