mike - i know. i always stretch the flats and i can see the various dust motes, etc. all i can say is that the lack of new flats was glaringly obvious in my old setup, and in my new setup not so much. i'm just really lazy and don't always take new flats. i was surprised that from the standpoint of a "visual" inspection, i do not see any changes over the course of about a week. in my old setup just a couple of nights would yield wildly different flats with overcorrection, etc. i'm pretty sure this is only because in my DSLR the LP filters are about 2cm from the sensor, and so any dust casts a smaller, darker shadow on the sensor. with the new camera and filter wheel, the filters are probably 4-5cm from the sensor. the donuts get spread out more.
i agree that the right thing to do is take new flats every day, but i'm just lazy sometimes. believe it or not i've even removed and replaced the camera multiple times and the flats still seem to work okay. i'm sure i'd get better results with proper technique though.
anyway WRT flats, the most important things are: flats per-filter and flats per-position angle, and as mike points out, flats per-time depending on how much dust you think is settling on your filters and ccd. the position of the focal plane at infinity is changing with temperature, so as far as i understand it, if you are tracking this temperature change then your flats should match subs taken at the beginning of the night as well as at the end of the night, because the flats also have been taken at the (perhaps new) infinity focus position. i'm assuming here that your focuser is doing temperature compensation. but even if it's not, just on first principles if this were a huge problem i think as you say there would be methods for dealing with it.
i've been using PI for like 3 years and the batch preprocessing script only appeared lately. it does work really well and i have used it but i just find myself reverting to my old ways. i really have to go in and read the code for the script to understand, for instance, how it calibrates the flats. i know the script includes some logic for seeking out darks that approximately match the frame being calibrated. but since flats are relatively short, i think a lot of people calibrate their flats with a master bias only. it's this uncertainty that keeps me from using the script more often. if i do it myself, i know exactly what happened.