How do you keep track of your income and losses. In particular from things like dividends? It seems like there must be a lot of stuff that needs to be provided to the accountant. Obviously this only applies to the unregistered investments.
How many hours a year do you figure you spend on this?
Most of our personal money is in registered accounts, so as you say that isn't a problem for paperwork or for tracking.
The vast majority of our unregistered funds are in the form of retained earnings in our CCPC. I have made that easy on myself/my CA by only holding three things. GICs and two ETFs (VTI and VXUS). It is very easy to calculate the GIC interest and the ETFs only pay out dividends quarterly. Once a year I provide a one page recap to my CA (along with copies of the TD statements). Easy peasy. That part takes maybe a few hours once a year.
Like I say, the unfamiliarity at the beginning is the hardest part to get over. Trust me, I spent many years procrastinating. I opened shop in 2002 and didn't really get my act in gear until the recession. But once you get past that and have it set up, it runs pretty easily.