Here's a logistical thought:

After realizing that i was spending too much time thinking about this stuff, I decided this month to make a simple checklist of vehicles that I know how to work (or need to work, in order to avoid a fee or whathaveyou) and put it into a spreadsheet so that I can check off when (and, if applicable, how far) I've driven each vehicle each month. I've also incorporated all of my CC closing dates into a unique calendar in googlecalendar, so I can see at a glance when statements will be closing (helps for putting that .99 charge on my otherwise unused chase cards, or paying down that 10k amex bill to $25 before the statement cuts, etc.). I still check in here often, but I'm having fewer of those moments at the end of the month where I wake up int he middle of the night panicking about whether I maxed out my BB for the month or remembered to use my AP, or got all 10 debit uses for my rewards checking, etc.