1) Certainly the frequency would come into play to some degree. You could inject 1X per week probably indefinitely without too much worry. If you are running 4-5 days a week, then the 4 week on / 4 week off is pretty safe advice to follow.
I typically inject 3-4 days a week in 5 week on / 5 week off cycles. The most important thing is to monitor yourself at all points when using insulin. If you have been monitoring yourself all along the way and keeping a log, you will notice if the time comes when exogenous insulin use is not effecting your BG levels as it has been in the past, which could possibly point to insulin resistance.
It is also important to use just what you need. For the majority of people 8-15 IU's of insulin post workout on workout days only is all that you need, but I can't tell you how many times I have ventured to various forums where you will have these yahoo's talking about using insulin 20 IU's at a time 4 or 5 times a day everyday for a month .... these are the folks that create the horror stories that we hear about, not the ones of us using insulin properly for bodybuilding. Even 300 + pound pros can usually get by with using around 20 IU's a day on workout days only of slin.
Overuse will only cause insulin resistance. Your body is only able to utilize so much sugar and will protect itself from high insulin levels by building a resistance to it in constance presence of supraphysiologic levels. Sugar is actually a toxin to the body above the amount needed to fuel the brain and glycogen for the muscles. That is why diabetes is such a dangerous condition. Sugar levels above the lower 200's mg/dl for any length of time will kill off your small blood vessels, damage your kidneys, and in general start killing off other organs. That is why insulin is such an important hormone. It is your body's only defense against sugar buildup in the blood-stream.
2) A non-insulin user wouldn't have to be concerned about their post workout dextrose shake assuming the rest of their diet is clean. The problem with today's society is that we live in an age of super-refined foods - flour, sugar, high fructose corn syrup, etc. are the primary ingredients of TONS of the food that we buy.
If your diet includes a bunch of the typical garbage that is in most supermarkets and quicky-stops, then you are almost certainly already insulin resistant and on your way to type II diabetes whether you realize it or not. In this case, a post workout dextrose shake probably won't even result in a insulin spike at all .... the pancreas has most likely burned out and given up long ago.
A typical bodybuilder is more careful with their diet than the average person though. We eat fresh vegetables, fresh fruits, and clean, fat free meats whenver humanly possible. In our case, a single shake a day of dextrose will spike our endogenous insulin level and get that dextrose to our our muscles to refuel glycogen stores after our workout and start the healing and growing. It won't cause a problem with the 3-5 times a week we workout to use this shake over the long haul.
If our diet is crap then certainly some time off would be in order .... but that time off should include time away from all the other sugars and super-refined flours and other insulin triggers as well.