It probably has a guide plate that makes it necessary to be within 12 degrees of straight on to hitch easily (makes me think it is a PullRite Slider hitch). This does cause some irritation when having to use an off-level/short site that has the tow vehicle at a severe angle to the trailer. Does he have a short-bed pickup?
As to the overnight setup--that is a personal choice. We hardly ever used the jacks down when overnighting, just got used to the movement. The rear screw jacks don't have to be replaced, just use a cordless 20volt drill with the matching socket--amazingly easy/quick. However, when overnighting, the front jacks can be set to the ground, as can the rear jacks, for stability. I do this for front-to-rear leveling when overnighting--you just shouldn't lift the trailer to the point where it begins lifting the truck.
Again, if the deal is right, the units are right, a complete setup can be a great starting point to having what you need. Plenty of people find themselves in the same situation which results in some nice package deals if you can be ready when they pop up.
Joe