I would not "blow out" the air filter. Doing so can "re-arrange" the filter media and provide pathways that will allow more dirt to infiltrate than if the filter was left alone. A dirty filter will "filter" better but flow less. If you are looking to keep clean air going into the charger and maintain "close" to new filter flow and wish to maintain the air filter on your own, I suggest placing the little brush on the hose to a shop vac (you know the one that comes with most all vacuum cleaners). If you don't have a shop vac, you can borrow wifeys when she's not looking. Rotate tires and change air filter when it's beat, or sooner if needed.
Since you run synthetic oil you "can" extend oil change intervals (supposedly) to twice the normal length. I use regular Rotella and change oil & filter every 3k. A friend of mine uses synthetic and changes his every 3k. Whatever suits your style - I guess. However, I noted that you pull a trailer 50% +/- of the time and you probably could put 3k on your truck in 1/4 the time that my friend and I do. So, with this in mind, I could suggest changing the oil filter every 3k, of course fill the filter up before installing it w/fresh syn oil. Then I guess if your loging 6-9 k miles quickly = 1-2 months you could change the oil and filter @ 9k intervals. Remember, most people don't realize "stop and go, short trips/driving in town" = severe duty maintenance schedule. If the majority of your miles are highway, even if towing, you should consider your truck to be "not severe".
I do my trans annually, but I don't put a great deal of miles on it, you'd be OK @ 24k and adjust the bands too. I would use a synthetic gear oil since you tow and change it when you do the trans. Some folks use a higher than recommended 140W gear oil when towing, but if you are in an area where temps get low I'd suggest staying with the recommended 75/90W oils. Especially if you are changing it every 24k or so.
Now the coolant. I try to do it every year but am behind by about 10 months

So I'll be doing it this Spring. About every 24k miles. You'll want to disconnect the hose from the heater core use it as the drain and connect the garden hose to the head. Be careful not to "Blast" the garden hose pressure - the coolant systems usually only see 15 - 17# - check the rating on the cap, if you go blasting 40 - 50# of household pressure into the system you could be looking for trouble. Make sure you open the drain cock at the bottom of the radiator before disconnecting any hoses and let it drain into a collection container, leave it open as you flush and let it drain until it stops when done flushing. Another recommendation is to go to WallyMart or the like and get "distilled water" to do your 50/50 mix as it won't have all the crap tap water does. Oh, stay away from those "long life" coolants, especially that orange/red garbage they use in GMs, long life coolant = shortened system component life. But, I guess you could always keep re-using the coolant ($6/gal) after replacing the radiator/heater core etc. (Big $$$ per part) :-laf
Check the shock absorbers for signs of oil leakage every oil change, grease all zerk fittings on front end and shafts every oil change and check air pressure "cold" weekly.
Sorry for the long post, I woke up early and have been cruising the net since 5:30 - ON A SATURDAY! hope my suggestions help.