I'm in exactly the same situation. I have 2, maybe 3, days of grace after the meds run out before things go bad. There are two things I do.

1) Use a mail order pharmacy where you can order a 3 month or more supply at one time instead of monthly refills. Your insurer probably has a program like this since it's cheaper that way. This will cut down on the low supply periods (<1 month reserve) from constantly to 4 months a year.

2) Have your docter order larger doses then required for that 3 month period and cut them down. Reorder when there is a 1 month supply left. This means you will always have a 1 month reserve. I'm not entirely sure of the ethics of this, but unless you are talking about the abuse prone drugs (i.e. oxycodin), I don't foresee a problem

NightHiker: Not to chew on you, but I should point out that some of the more common perscription (e.g. psychotropic drugs) don't have OTC or homeopathic equivelents. Going off these in the middle of a crises is about as much fun as sticking your arm is a blender.