Check the outfitters references. If he sounds like a good one and he has a good area that is the way to go if you can afford it. You will have a much better chance at being successful especially as it sounds like you may not have much elk hunting experience.
$2000 sound a little high, drop camps here in Idaho of that nature run in the 1400 to 1600 dollar range.
If he has a good area and is going to drop you back aways from the bulk of the pressure you are much better off with the drop camp.
Taking care of an elk after it is down is difficult but just think of it as a large deer, basically the task is the same. If you get one down on a steep slope by yourself it can be a real bear trying to move it around for cleaning and getting the cape and meat off but it can be done. I have done several by myself.
If you get animals down in a hole it will be worth the price of the drop camp just to have the horses to pack them out.
Have a great hunt either way.