Sounds like tax evasion to me.

Type TFSA in google and check out the govt website. They do a pretty good job of summarizing and keeping it light. After reading it about 3 times I felt I had grasped the jist of it.

They are changing some rules to catch people from doing things that sound similar to what you are talking about. The key word in your case is 'arms-length'. You are not arms-length from yourself so I think that disqualifies you from selling to yourself.

Just some thoughts to get you going but I think they've got your strategy plugged. I do think there are some other 'loop-holes' that can be exploited. Not the least being putting highly speculative investments in it in order to create room inside your TFSA that cannot be taken away from you.

Probably several other loopholes and we probably only have another year before they change the rules on us....