Hey Jack! You may want to consider a late 90's Chev suburban 1500 4x4. These can be had for well within your $5000 budget. Most of these things you will find will probably be loaded with all kinds cool stuff, power everything. Equipped with a 350 v8, you will have more than enuff power for towing and taking along a few family and friends. Lose the third row seat and fold down the middle ones and you will have (leave the family at home) cubit footage that rivals any 8 foot bed p/u, and the cargo will stay dry in inclement weather. 4x4 for sure and you will be the king of the road in the deepest snow. I use a '99 burban 2500 with a 454eng. Waaaayyy more than enough car that I need but all worth it.