How's the road to beaterville coming anyway?
To be candid dude, if you get your truck on 33's with the OME 50mm lift, a good front bumper and a winch.... then you'll be in great shape and there would not be many trails you could not do. Yes, bigger tires and more lift = tougher trails, but you can have as much, or more fun on intermediate through advanced trails too. Plus, more of your friends and club members are more likely to run the moderate to intermediate trails rather than full hardcore. Take it one step at time, starting with purchase of a truck, then going a lil here and a lil there. You'll be fine.