I mostly blow mine out due to mowing kicking up so much chaff, like we've all seen happen. When I'm moving dirt (or snow in winter) there isn't nearly as much issue with "stuff" getting into the radiator and cooling fins. I've just made it an automatic part of my mowing chores that I have to clean out the fins. When I'm out running the tractor (mowing), I'm constantly watching that temp gauge. Under normal (as in the coolers/radiator are clean) the temp gauge is pretty rock steady and doesn't climb even when the day gets hotter, say comparing mowing in morning, vs. mowing in afternoon. But what I've become accustomed to is if I see that temp gauge suddenly start moving higher, that means the fins are starting to get choked with chaff. I will stop then and blow everything out. Sometimes that takes several hours before I see it change, and sometimes it will be an hour or less. Depends on the field I'm cutting, and how much "junk" is in the air.
I also blow it all out when I stop for lunch (mid day) and anytime I have to stop for fuel refills.
Sometimes you get lucky, depending on the field, little to no seed heads or pollen, and you can go half day or better. Some fields are bad and you're stopping every hour or so. Cattails are bad too, if you're stuck cutting a bunch of those, they are little "chaff-bombs". I really don't like cattails. I'll try to back into those if I can.