As long as you know/trust them there's no reason you can't.

You could also just roll up a f2p mule to hold your money/some items for you.

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Thayet
@thayelf // http://thayette.tumblr.com

"But you must know that if corruption is powerful enough, it's not corruption at all — it's law. Unspoken, unwritten, but law." — Robert Jackson Bennett, City of Stairs

>>The reroll mechanism in place is to specifically strip off a character's coins, so I don't know if circumventing it is an entirely above-board thing to do.

I think you are reading too much into it. While you probably won't get a GM/GH to tell you to do that they aren't going to come down and take all your money/stuff and slap you with a warning if you do. They are aware that people want to keep all their money/possessions if they reroll a character and are ok with it. I'm pretty sure I remember GMs telling people to hand their stuff off to people they trust/another character in the past in this situation.

Also, I'm pretty sure the reroll mechanics haven't been touched in 20 years other than to make sure they work when they've made big updates. I'm sure there would be options to keep your stuff if it was completely rewritten today.