Canada’s most generous charitable mechanic — the elimination of the taxable capital gain on an in-kind donation to a registered charity — applies to publicly listed securities, mutual fund units and similar, not to shares of a private corporation. Donating private company shares instead engages the non-qualifying security rules, which can defer the donation receipt until the charity disposes of them.

So this mechanic is unavailable to you until some meaningful part of your wealth sits in listed securities — which is, in passing, one more argument for the holdco layer in item 2 doing something other than holding cash.