RE: Target $200You seem to have missed the point. If you think WIN shares will EVER get to $20, then you are well advised to swap them out of your RRSP (not a withdrawal or cash out, just swap cash for shares) now (even better was at $1!). This way you will benefit from a much reduced ultimate taxation of the growth of WIN share price. The tax deferral is the same, inside or out. If you don't think they'll grow at all, sell them outright - don't swap.
Think of my example. You buy WIN with new RRSP deposit for $8,000. You get to deduct $8,000 from your income that year. A year later, WIN goes down to $0.01 a share. You swap at that time for $.01. A year later, your WIN shares value goes up to $8,000, but on a non-registered form. After capital gains taxes of $1,600, you have $6,400 tax free dollars! If you have left it in your RRSP, you only have $4,800 tax free dollars (assuming you can withdraw them and pay the same 40% taxes that I assumed you saved going into the RRSP with an $8,000 deduction). You are ahead by $1,600 tax-free dollars, and WIN's share price hasn't contributed a thing towards that gain (it is the same price you bought it at). How come? Tax rate difference on Capital Gains when held outside and RRSP versus inside. So who cares about 20 years? That only amplifies your benefit of swapping out now!!!!
Your only reason to not do the swap is you cannot afford to (ie you don't have the cash (or similar non-registered asset) to swap equal value with (say a bond or some real estate - any RRSP eligible asset).
In general terms, you should keep capital gains earning assets outside of your RRSP and interest earning within.
The hedge it provides you in this case (allowing you to have a lower WIN share price breakeven (or profit) point) is a bonus at this time.