I am one of those "short-run daily drivers". My daily trip to the bus stop is about 15 miles, with about 12 of it on the freeway at 70 mph. I am a "weekender" as far as camping, pulling my 5th wheel 6 - 8 weekend trips during an average year, with an occassional longer trip. In addition to my daily driving, I do many shorter trips around the area (I live a bit away from the "city life"). My last diesel had near 70,000 miles on it when I traded it for this one, and ran great and had no issues. This one has about 16,000 with no issues. I think as long as it gets its "Sunday drive in the country" every now and then, and it's properly maintained, you should have no problems with it. You mention diesel specifically, so I assume you have a trailer big enough to warrant the diesel. Are you planning on "seeing the country" after you retire? If so, I doubt the shorter trips between pulls will be much of a factor.
My 2cents and personal experience.