While I have off-road experiance in 2wd's, this will be my first time with a 4x4...
I would prefer the easier trail just because I am not going to be Mr. "I am a pro" and risk breaking something for no reason... Nothing wrong with starting out easy and working your way up...
2wd's are actualy harder I think because everything must be done with speed and power rather then slow, brute force... I can't even recall how many times all 4 tires left the ground at the same time on my XTerra.
Out of about 5 off-road trips I got stuck only twice during those runs, all the other 4x4's were suprised just how capable that little truck was for a 2wd...