It's all math and when you do it the cost saved is never what think it is. Around Raleigh diesel costs about 15% more per gallon than regular (
http://www.raleighgasprices.com/) so you need at least a 15% increase in mpg to break even (assuming equal payment or no payment).
you say 50 miles per day x 5 days per week x 52 weeks = 13000 miles per year. Lets say you put an extra 5000 per year on the weekends for a total of 18000 miles per year
In your current truck 1285 gallons of gas per year at around 2.70 per gallon is 3469.50 dollars per year.
If you can average 20 mpg in your new diesel that would be 900 gallons of diesel per year at 3.10 dollars would be 2790.00 dollars per year.
so the difference is about 680 per year, 56 dollars per month, or 1.86 per day.
So depending you personal finance situation that might be enough to justify, but it seems like most of spend more than that per day on coffee and soda.
Those are pretty high miles per year to me and 20mp on an average is pretty generous (my 12V cummins with a 5 speed and 4.10 gears only sees 19mpg on the highway at 1900 rpms and averages around 15-16) so real world savings will probably be less per year. When you look at with 18mp the yearly savings goes down to 369 dollars per year.
If you just want a diesel then go for it, but fuel savings is rarely the reason.
If you need to save 700 dollars a year to get by you should drive yugo or ride a bike.