When I go to work I park my F350 next to the daycabs in the lot. The dually makes me the same width and because to the "twin screw" (double axles) the class 8 beats me by about 2' in overall length.
As for maintenance, HDT oil changes are every 40,000 miles and a non oil change PM is every 20,000 miles. You can run oil sample to determine when you actually need an oil change. Oil change is about $250 vs $100 for the pickup. Which based on interval the HDT may actually be cheaper.
Please don't confuse the new "tow war ratings" with what a MDT is capable of. The MDT is built to tougher standards to do it's rating, day in and day out and last up to a half a million miles or better. The "pickup" can't perform to that level. While you'll wear out a pickup, I doubt you'll wear out the MDT/HDT.
Step height is an issue, although there are alternatives. It's one of the reasons keeping me from buying a MDT/HDT is my partner's bad knees. But a set of rear steps and a door in the back of a HDT cab, may be a work around. I also like the F650 conversions with the air ride. A compromise for us may be an air ride conversion, which I believe Ram will offer in the next year on the 3500.
There are pros and cons to all the options. The research is cheap and can be fun. Keep your options open ;)