Chronically low air pressure

You would think that at some point I would realize that it's a benefit to me to monitor the pressure in all of the tires in my life.  My car tires are always low, it has one of those stupid warning lights to tell me that a tire is low but doesn't tell me which tire.  To make matters worse, the warning light NEVER stays off for more than 24 hours, meaning it's like the boy who cried wolf.  I ignore it, that is until I'm loading something in the car and realize "oh shit, I almost have a flat".  Now, the job of monitoring the car tires is Joe's, so it's always his fault when I'm at the pump filling them up in the pouring rain with the kid screetching in the back seat...it's always his fault...lets not discuss that he maybe drives that car 4 times a month.  Moving on, there are the good old bike tires that I also neglect.  I don't get along with our bike pump, it could be user error but I really think the pump sucks, so my tires are rarely inflated to where they should be.  I know, I know, this is a problem...a problem I can deal with after the big race b/c the morning of I plan to have the bike support people use thier fancy compressor and make sure I'm in a good place.  Then we land at the tires on the jogger...yep...both back ones were flat today during my run.  They were likely also flat for my last SEVERAL runs...again I never check them.  The worst part of it today was I checked them after driving to Lincoln Woods, after hauling the jogger out of the trunk, after loading the protesting child into the stroller (who was bribed with some cookies..Mom of the year over here).  Where was the pump?  At home, I took it out of the trunk this weekend.  I ran anyways.

Ran 3 miles.