I think we are getting a little over board with the weight here.
Unless he use the M12000 (136 lbs), the other warn are all lighter than that (98-100 lbs) but still heavy. + the mounting plate probably a max of 150 lbs. But I do not think he need to pull the complete kit out of the truck to use the winch. At least not on the same lift. I do not like them, but he could use synthetic line to reduce the weight.
As for using the cable under the truck, this will put a lot of strain on the lower fairlead, rollers have a much smaller diameter than a snatch block, all that also depend on how the bumper is built so the wire will not rub againts any sharp edge. (forget about the syntetic line). Also maybe it is easy in Arizona sand, but forget runing a line under the lenght of a truck in deep mud or big rock.
As for angle pulls, he can always use a snatch block on the other side of the trail to realign the wire that do not have an ancor point in the middle of the trail.
And for a final tought about winching, if you need the full strengh of your winch to pull you out of trouble, Maybe you should look Under your rig to see if you are not hook on something big. A recovery operation need good planning and thinking to make it safe and efficient. But we all know that wright!
As for the rest, they are good argument about different option. They all have good and bads regarding what you want to do and their will ben more. That is all part of your reflexion.