Make a list of what you want to achieve and number them 1- 2- 3 in order of priority to you. Be honest. If ride comfort is #1, let it be that. Or if it's the money, let it be that. Once you've made the list, ask yourself which option fits #1 (whatever it is) the best. That is probably your best option to take.
The thing is, there is no right or wrong answer. Only shades of gray (way less than 50, lol), because no one can see the future... so any change we make is a roll of the dice to some degree.
If commute comfort is #1 priority, nothing beats a separate commuter vehicle. (BTW, have you test driven an ecoboost with the HD package? Don't assume what the ride will be like.) And if the fuel savings pays for nearly all the expenses of that smaller vehicle (amortized over the vehicle's expected life, not just over the payment period), when you add in the lower wear and tear on your F250 you may actually come out ahead. Don't forget to add in the somewhat higher repair costs if drivetrain work is ever needed on the diesel.
