You might even want to apply and lock in non-cancellable DI before you go too far down that route. The reason is that (as I understand insurance) there is an obligation to disclose material information to the insurer. If you were on the brink of quitting your job any moment, I think it might be dishonest to get DI at that point - or you should at least disclose the intention.On 1., this is a good point. I am working on some side business ideas. If they develop into something sustainable, I will look into such DI prior to leaving my current employment.
On the other hand, getting DI well in advance, back when you are still in the 'regular employee mode' seems perfectly honest. Again make sure it's non-cancellable and beware of the categories like 'any occupation' vs 'own occupation'.
You're absolutely right, and if I remain on this track, I will end up with less CPP than most Canadians. I'm glad you reminded me. Missing out on CPP is a pretty unfortunate consequence of reducing or stopping my employment income.The other downside is that you have less 'pension' income due to lack of CPP contributions. That gives you more sequence of return and rate of return risk. You seem to be quite a saver, so maybe not a problem, but something to consider.
Do you think it's possible the government may let Canadians buy into the CPP, contributing extra? On my current track, I might not get anywhere close to 100% CPP, unless I go back to a regular office job for a few more years.