Well because data persistance is not as reliable as datastore, i would use datastores.
I would create an ID for each sword, hat, gear, staff, or whatever, and each ID is unique.
Then, I would create a string value inside the player called "Save".
Then, I when a player enters, it loads the string value, and inside it, it would have the data.
ie: "1,3,15,95,101"
and then use some string doodas to pick out the numbers individually, then give the player all the items based off of what number to use.
PS: what I mean by doodas is this:
http://wiki.roblox.com/index.php?title=String_pattern
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How would I go about picking the numbers around the string? The Wiki doesn't really help with picking the numbers out and doing things with the numbers.