china56 asked:
"Now heres a question - when are the proceeds of the sale of shares held for less than 12 months deemed to be income and not capital gains?? Is there a rule of thumb that should be applied?"
That will depend on the status of the trust: whether it is a trader or investor.
On using a company as one of the beneficiaries, I had mentioned before that a company, as a beneficiary of a trust distribution, cannot be the ultimate beneficiary, meaning the income retained in the company has to be distributed to the ultimate beneficiary eventually. I think you have got that piece of advice already, but do check again on the timing of the distribution to the ultimate beneficiary by the company; I don't think you can withhold distribution indefinitely.
Just my opinion, not a advice.
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