If we are talking CJ-5 I would want an 8,000 lb. Warn winch myself. If it is an older model Wagoneer or something in that realm I think a 10,000 lb. would be more appropriate.
Don't forget a roller fair-lead (sometimes included and sometimes not) and be aware that he may need some form of...
You need to practice, that really is the only way. I can give you one tip though. If you don't have a convex mirror on the right side, get one. When you can see the curb and the rear tire at a glance it make life worth living...