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If your friend keep it up, he would not pay any taxes for awhile. It is kind of difficult to pay income taxes from jail. But let's not give the IRS any ideas, or they may want to tax him in the value of the accomodation in jail.
After all, it is not such a bad idea !!!!! It will save me some of my taxes that are used to keep others rent free ( and income taxes free too ).
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