If it's done that way buy regular account with say 7k this week then transfer in kind on Jan 2n to his tfsa, agreed it's deemed disposition sale but he may not incur any taxable capital gains if is ACB is higher like most of us even if he's up on those few 7k worth shares. He  won't be able to claim carry forward loss though given bought and sold within 30 days between accounts ( as always open for corrections. Cra ain't easy to navigate)