I built software some time in 2003, and I've tracked almost every transaction in all of my accounts since then. I even used to track my escrow accounts, but I managed to convince myself that I don't need to do that.
I check my bank account at least once per day. Sometimes more often, but there's almost no point because stuff pretty much either shows up in the morning, or it doesn't. (Some things do seem to hit later in the day, though. And car payments happen right at 6:30 PM. Mortgage payments happen at 9:30 PM. If I prepay my mortgage, the money leaves checking instantly, but only comes out of the mortgage at 9:30 PM.)
I check my 401k every Wednesday just to confirm that the most recent contribution/match has landed.
I don't look at my IRA/investments much any more. I used to all the time. Now, I generally just check them quarterly (i.e. early October after 3 month statement comes in) and I then log any dividends, fees and change in value to my software at that point.
I tend to check credit card accounts often - not quite daily. (Usually not at all on the weekends.) I manually keep track of all transactions in my software.