I track all my spending with my phone app: Spending Tracker (its free and good)
I have roughly 30 categories, (and you can add whatever you want).
I always have my phone with me and it takes 15 sec to enter a purchase at the end of the day, so easy it doesn't bug me.
Each month or two, I transfer the monthly summary to a spreadsheet so I have a history and can chart it and compare to previous years.
I make a new tab each year, copy the previous year and delete the entries to have a fresh identical new year to start with. This way I have multiple years each in a tab.
Separately, for my rentals, I use a spreadsheet, separate tabs for: rent paid, rental expenses, rental CCA. I don't find it hard to track that way.
Harder to me is saving all the little receipts (I currently use separate yearly envelope, but am thinking I should take photos of the receipts in case the receipts fade away over the years).