I would say if the loss of the friendship would be acceptable, then go for it. If the loss of the friendship is unacceptable, best to just walk away from this one. I had permission once to do just what you are describing and like somebody mentioned above, ill feelings were lurking. Destroyed the friendship. Luckily the friendship wasn't something I really valued all that much and it actually all worked out to be quite positive.
Bottom line, from what you've described I wouldn't go through with this.
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