my .02...........
imho a reg cab truck is great for a single guy. once he starts a family, it now is an endangered species. if your truck was a ext cab 4x4 and you know you'll be settling down for real, I'd say keep the truck and teach the other half how to drive stick. I have proven to the ardent naysayers that a diesel stick requires almost no coordination to do the throttle and clutch.....except in San Francisco, CA. with the ext cab the truck can haul the family in a pinch and the loose stuff you don't want to keep in the bed on shopping runs can go behind the driver's seat. this is not an option with a reg cab truck. A crewcab is really nice for hauling family and friends to activities comfortably....boating camping, dinners...etc. but it is a bear to park especially when it is a dually in a urban area. My suggestion is trade plus cash for a ext cab 4x4 if you want to retain the practicality of a full size 4x4 diesel.
Exploders are not a good option especially the 4.0 v-6 family. ford has yet to build one that doesn't eat head gaskets at the 100k mark. even the new SOHC 4.0 v-6's haven't been cured of that habit. Plus the new ones require more book time to do the gaskets.
I love the older Exploders because they are a good income source for headgaskets and transmissions
most of those owners are ******* deep in payments or money poured into one and have no choice other than pouring more money into it.
Jeeps are OK but you won't get a sig other to do a winter commuting in one. another thing is the mileage on a jeep sucks. I don't know why but I suspect the height of the vehicle has alot to do with it.
hope this helps.