You like your Ford and it sounds like (reading between the lines here) that it's paid for so, to me, the issue is that you need to use it more. Any vehicle you get that's sitting to be used a handful of times is going to depreciate. If the story were tipped more to getting a less expensive rig meant going out more and enjoying life, then I understand it. What are the chances that in 5 years that 99-02 is too old or worn for you? It's then that the 2014 would be an 8 year-old vehicle barely in it's prime.
I like where your head is at! Getting a different truck doesn't mean that I'll use it more or less but as new as this truck is, it is definitely depreciating. If I were to get a 7.3 for example, it would depreciate much slower than the 6.7. I sold my '95 7.3 5 speed a few months ago. I had it for 6 years and put 70k miles on it. It actually
appreciated a few hundred bucks from where I bought it. Since Ford made 2 garbage engines (6.0 and 6.4) for 8 years, decent 7.3's will always be sought after at this point. That is, until you can buy a decent shape 6.7 for under $15k which I don't see happening for awhile. If I can get into a decent 7.3 with under 200k miles and only put a couple thousand miles a year on it, I don't forsee it depreciating much.
Having said all that, I am very interested in the 3.5 ecoboost after all of your suggestions and info. My dad has a 2015 3.5 that I'm going to hook up to my setup and see how it does. At this point, I'm not worried too much about the power to tow my 9k lb setup. I'm more worried about the trailer pulling the truck around too much. With airbags, appropriate tires, a good equalizer setup, and the long bed for max wheelbase, my research says that I should be good to go...and luckily there are a handful in the $20k range for sale.
Question: Did Ford change the ecoboost much between '11 and '15? Will my dad's '15 tow better than the '11-13's that I'm looking at? He told me that his is rated at 13k lbs towing and the 11-13's are rated for 11,300 lbs. Is that due to suspension or frame differences? Or engine mods?
Thanks for all of your suggestions guys!
I'm also looking for a 6.2 to test drive. there just aren't many of them for sale under $20k at all.