To be honest - seems like all your issues could be resolved by giving him the billing info so the card rebills automatically... People pay bills like this all the time, and you can always dispute it with your bank if someone over bills you. As for monthly payments - hey, that's the nature of subscription based software. Using subscription based stuff reduces your initial investment since you don't have to buy software for a lot more, but in the long run becomes less worth it compared to buying software straight out.
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