AutoADD: big new truck, bigger used truck, or stay home?

As AutoADD is much like addiction, never cured but always waiting for a moment of weakness, I'm thinking of shaking up the fleet again. Right now I have a 2000 F250 7.3 4x4 XLT extended cab as the house truck and water hauler and a 2012 Subaru Outback 2.5i as a DD. Average commute is 2500 miles a month. I also need to be able to haul fresh water to the house, which is mostly the F250's job.

While there is no logical reason for it, I dislike the Subaru immensely even though it's quiet, competent, gets good mileage, and gets me out of my house on the mountain in the woods without any drama no matter the weather.

The F250 I love, despite it needing more suspension and brake work than I have the time or free cash to fix right now. To me it's only real flaw is it doesn't fit car seats well enough in back to DD it... Plus it only gets 14.4mpg. I have an offer for it for roughly 3x what I paid for it, which is prompting this thought train.

Option 1 - The Subaru is rated to tow 2700 pounds with a braked trailer. Install a factory hitch and buy a water wagon (think a 5x5 trailer with a 200gal water tank on it). Life continues as normal. I do worry about its ability to basically pull a load at its tow limits 2-3 times a week will wear on it however, and my driving ability at pulling a heavy-ish trailer on narrow icy mountain dirt roads to get to and from the house.

Option 2 - trade the Subaru in for a new F150 extended cab XL. Reset the never ending car payment calendar, drive a relatively nicer vehicle, hopefully get it without too much negative equity due to all of the incentives out now. Leaning towards the 2.7l ecoboost. I am worried about how much hauling 1600 pounds in the bed 2-3 times a week will wear on it, if not 2000 pounds if I decide to overload it and get a 300gal tank.

Option 3 - go full retard on the truck side, buy one of the fleet turn in 2012 F250 XL Crew cabs long bed with the 6.7l diesel for $27k and 50k miles at the local used car mega store. Less fancy, no worries about overloading it, but way more truck to drive daily and no warranty. I don't mind parking in the way back at the store I guess? Get my big rah rah truck fix for a few years though...

Thanks for reading if you made it this far. How would you approach this situation?

Sounds like you should get rid of the Subaru since that's the one you really dislike. My friend bought a 2016 Ecoboost F150. Don't tell him but I like it.

Would you use the amount you get for the F250 plus the Subaru trade in on your potential new truck? Also, what kinda gas mileage do you get with the Outback? The F-150 might not be too much of a mileage hit if you go with the 2.7 Ecoboost. Could you fit a car seat in the back of the XL F150 extended cab?

Decided to just keep the Subaru in the end. Part of the reason to sell the truck was to reduce our monthly overhead, along with the nice big check for the truck, and any other vehicle option with similar capabilities as the Subaru or the f250 either results in higher insurance, bigger gas bills, or both.

Side note, backing a trailer down my driveway wasn't as bad as I thought it was going to be, a major part of my decision to keep the subie.