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The flash drive thing is okay for awhile, but by the time your save is 30K files and 0.8G in size, it becomes a real hassle. I used to have the data folder on a flash drive so that I didn't have to transfer files. I could just plug the flash drive in and start OOTP and it would work. The downside to this is the speed of the game really suffers running off a flash. Eventually I just designated one of my laptops as my OOTP machine and stopped machine hopping.
One thing that would help would be if you could set a network drive as the data location. That way folks with cloud drives could just keep their data on the cloud drive, or you could keep the data on a desktop computer and point your mobile computers to that location.
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