I go every year. There are a lot of places to stay. Honestly, if you are going with a group, look into house rentals. There are some nice homes that get rented to the public, for just a weekend/week long stay. You can have a pool and all for very reasonable. I have been staying at the Moab Rim Campground recently, just on the SE edge of town. They have nice affordable cabins for 2 up to 6 or 7 people. Its good in the off season, but I don't know about the busy season –what I mean is that they don't seem to have an urgency for putting money back into the place. Last time I was there one of the bathroom stalls was out of order. No big deal, UNLESS the place is full and you gotta ****! :****: It was closed off the entire stay and nobody was working on it.
For a little more domestic, I have stayed at the Virginian Motel and had great experience every time. It is walking distance to everything, Moab dinner is right around the corner, as is Woody's Tavern. The streets are WIDE, so flippin a bitch with a trailer is no big deal. You need to be careful driving back in the eve, if you've been to the bar, so walking distance is always nice (No DD necessary) For brews and good times, I have to recommend Woodys and Frankie Ds. More like a local saloon then a touristy bar. Occasionally you find some businesses in Moab that have forgotten what keeps them there. I have had a couple very isolated incidents with poor/rude service at restaurants, but Its not the norm. All of the out of towners are a double edged blade for the townys. Most of the food in town is surprisingly good.
I cant help you on the Jeep rental. I have seen plenty of them along the main drag, but never used their services. Good luck. Even easy trails and not so perfect days are awesome in Moab. It is Heaven on earth.