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What to order? A new loaded diesel Overland, or base diesel Rubicon?

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In Florida. Not a big off-roader since my youthful days. will be doing light construction out of it during the week and hopefully getting topless , doorles, beach, etc playtime on the weekend.
Not a real max options type but the overland has a sweet package deal and it may be more suited to my general needs, but...

I really like the idea of having the flagship trim and the off-road bug may bite again. So what are the short/ long term pros and cons with each? Will the capabilities of the Rubi over the Overland make a difference in some of the Ocala Nat’l Forest trails, and those to be had from S.FL to North? Assuming light use, which would hold its value better after 3-4 years? Is there another aspect I’m overlooking? I will most likely NOT be modifying it beyond a 2” lift and 35s. No winches, etc. It will get a bed topper and rack, and it’s possible the rear seats will come out for tool storage.

IOW, talk my heart out of getting the Rubicon, like my good sense is telling me to, lol.
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I’ll never use the 4 to 1 transfer case, I plan on adding new gears and locker later so I went with a diesel overland

then again I did this at 1500 miles, would have been sooner but was waiting on wheels

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kooltoys

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didnt think I needed lockers when I bought my JT.. Hind sight, Should have at least cost compared pricing on a Rubi. but I knew nothing 6months ago, still don't but love my truck
 

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I'm in the mindset of rather have it and not need it. Also the Rubicon will hold value better and I think they just look better than the overland trim.

BTW I ordered a diesel rubicon and waiting for delivery now.
 

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didnt think I needed lockers when I bought my JT.. Hind sight, Should have at least cost compared pricing on a Rubi. but I knew nothing 6months ago, still don't but love my truck
Have you found yourself in need of locking differentials?
 

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Have you found yourself in need of locking differentials?
yes sir, you have not really tried til you get stuck, right! I could not climp that wall and didnt want to lay my brand new truck in the rut, so I tried a mud holes and sank. locker may have helped as I lost 1 if not wheel s traction

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Me with lockers in a shallow dip which I thought was dry, and a sandy hill.

I think in most cases winch > lockers.

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