Off Market, page-205

Yeah I getcha - I don't pretend to know the situation in depth, was more just answering some of the previous points from others comments as I saw them. Haven't paid particular attention to the proposed buys/sells. Your points completely valid, to play devil's advocate though: if the OP is talking about utilising losses, then they must exist somewhere between buying back in and current price. And depending on the actual gains vs losses, it might be possible to at least considerably reduce the tax payable even if there isn't cash changing hands.