Hi Mvls, I'm in a similar boat on some positions in the trusts so what I do, for tax reasons in the US, sell the highest priced shares, that way my average price per share goes down after the sale and I get a tax loss against other income. It took me quite a bit to figure out this approach but it has helped keep the taxes the trusts pay to a minimum and last year got a small loss via K1s to the beneficiaries which helped their taxes as well.
The average return on the positions in the trusts on original purchase price was ~9.8%, dividends and sale gains. Though a somewhat complex approach I have been able to dig my way out of the worst of the positions that my mother's broker put her into. His logic, it seems, was she needed income more than stock appreciation given her age. Not totally unreasonable but it left me with some halasish paper losses to contend with and yet significant taxes for the trusts and not a lot of spare cash to pay the taxes with. Doing the sale of the highest cost shares brought in the cash and losses to offset some of the taxes at the same time.
Plus, it made it possible to start AIMing positions such that more reasonable buy and sell prices were there. In once case I would have had to wait until the stock more than doubled to get a sale if I simply used original purchase price as the AIM starting point.
Best,
Allen
