I've done it this way twice but I have a buddy with a big rig and a 3-car trailer so that part was easy. The rest of it can be a challenge if you're on a budget like me.
You can fly into and out of Moab, they finally have commercial flights 2x or 3x a day but they can be pricey. The airport is about 30 miles north of Moab so you'll need to figure out ground transportation ahead f time. Renting a car for running around town is extremely convenient but there's only 1 car rental company in Moab, Nation Car Rental I think.
If you dont fly into Moab you basically have 3 options: ABQ, SLC or Grand Junction and then rent a car for the week. Al boils down to how much $$ you want to spend.
Each time we went for 2 weeks. in 2015 I flew into ABQ and few out of GJ. I was lucky enough to be able to catch a ride each way so no car rental was needed. Last year I flew into Vegas and rented a car for the entire trip ($235 total), drove from Vegas to Sand Hollow and wheeled for 4 days. Loaded back up and wheeled Moab for 7 days. On the final day I watched the big rig drive off from Moab and I turned the rental around and drove back to Vegas for my flight home. Was an epic trip!!
You're going to find that renting a one-way car and dumping in Moab is expensive, thus I just kept it for the entire time. There's A LOT more involved but you get the idea.