I purchased the Off-Road Premium Gas model with tow package. I chose this model for the off-roading tools (4-wheel drive, rear locker, multi-terrain select, and crawl control features. Also for the Tech (Larger screen, panoramic cameras, power lift-gate, integrated brake controller/straight path assist for plug & play towing, heated seats/steering wheel, ventilated seats, and digital rearview mirror, etc.)...these are great comforts for daily driving and when the wife and I road trip/tow a camper. With overlanding in mind, I imagine your first mods will likely be some type of suspension adjustment, new wheels/tires, and underbody protection (skid plates/rock rails), so these are things to consider as they are costly. Many folks might choose to use the $9K you mentioned for those upgrades vs. spending it on the premium features.
Regarding powertrain...I didn't choose the hybrid because I was able to hear a constant, high pitched electrical sound coming from underneath the center console area (most likely from the dc to dc inverter) and it was too annoying. That, and the loss of cargo space and higher cargo platform from the batteries wasn't my cup of tea. But if you can't hear the sound, and you don't mind losing some cargo space...the extra power of the hybrid powertrain is said to make off-roading a bit more controlled/smooth since you have so much available hp/torque...especially if you've got lots of gear. A drawback is less load capacity due to the weight of the batteries. For me the ORP was worth the extra $$...especially since I wasn't going to do a bunch of big mods right away. If you don't care about the extra tech features, a standard Off-Road with the hybrid powertrain might be good compromise. Good luck with your choice and all your adventures ahead!