The only functionial off road difference between the Pro and OR is the suspension. My understanding is the Pro's suspension provides a smoother ride at higher speeds while off road and no advantage while crawling around. So unless you are going to drive at higher speeds off pavement, the Pro doesn't offer an advantage.

The only thing to be worried about regarding modifying the vehicle is catching the bug hahaha. I think it's worse if you like to tinker.

Does insurance cost more for a Pro? I wouldn't think so, but it's worth asking your insurance provider.

OR: Cheaper out the door, cheaper loan?, best bang for the buck, mods don't yield ROI, possible warranty hassles?.

Pro: Drive and enjoy as is, Army Green!, cost more (out the door and loan), not as capable as a modded OR.

You can't go wrong with either trim level. Buying based on future resale value is risky as someone else mentioned. And, as another member stated, don't expect to recoupe any money spent on modifications which isn't a big deal if you don't go off the deep end. Shocks, rear spring spacers, tires, clone Pro grill, and valences, then call it quits. If the financial aspect is your highest priority, get the OR. A stock OR can go everywhere a Pro can and you will save money on the vehicle price and loan cost if you finance. I hope that helps with your decision.