The way that the winch would help out on a 2wd is that he will be able to recover himself if he got stuck like that again. Of course there has to be something that he can anchor off of within distance of the winch. He'll be spending a lot of money to get that. He's got to get a winch bumper then the winch, etc. You're looking at about $2k for that stuff. Then you have to include the amount that is needed for the lift kit then installation if he's not going to be able to do it himself. Over all with all of the money spent on it, it would be better to save the money needed to do a trade in and then have a 4wd truck. You'd also want to get better tires as well since the stock ones really suck.

2wd's will go pretty decent as long as you have good driver's skill and remember that momentum is your best friend. I wheeled my 2wd X with the 4 banger in it for two years before trading in for the new x so I know what it's like to only have 2wd. As far as slick surfaces you're not going to be able to go that far. The ABLS will help some but not take you as far as a truck with 4wd could. For snow and ice you're going to have a hard time especially if you have to go up a hill and have to come to a stop then start again.

If you're going to Alaska I would really take a hard look at the amount of negative equity that you have in the truck and getting that money together to do a trade in for something with 4wd. I wouldn't go up there with a truck that only has 2wd. You'd probably be stuck every couple of feet. Any other questions just ask. Hope that helped some.