To answer the question about the cost of capital gains exemption, the numbers you're showing are not regular. If you're a 44% Ontario taxpayer and you donate marketable securities to a charity, the odds are it's not going to cost the government 69¢ for that gift.
If your cost base is 50%, then it might be a cost of 56¢ to the government. In today's market you don't have very many gifts that have a cost base of under 50%, so I don't see those numbers as being the actual. Yes, there could be an outlying situation where you have zero cost base, but I don't see those numbers as really being representative of capital gains.
For the gifts we're talking about for private company shares, they're not getting those capital gains taxes. You're not selling those private company shares to anybody. No one is buying them, so there's no capital gain except on death.