Hi Courtney,
Unlike one respondant to your dilemma  Air vs Water,
I have owned & loved both:  A Splitty, a '69 Westy, & currently a
watercooled ('85) Westy.  I love all three!  And as much as I love & trust
my current Westy, who carried me safely & comfortably to mainland Mexico and
back with no trouble, I could easily own another Air Cooled.
    Like many, I'm no mechanic.  But my intuition re which vehicle to buy
has always served me well.  My three Westys always provide dependable,
economical, & nearly trouble free service--because I chose well, loved, &
maintained them carefully.
    One thing I miss--long for even--is the "soulful" sculptural form of the
older vans.  What Vanagon will ever equal the beauty of a Splitty, for
example, or even a Loaf?
All other things being equal--go for what you like.
Find a van that just "feels" right.
I bet you know what I mean.
For fun, check out  www.vintagebus.com
Good luck, & have fun!
Ciao,
Phaedra
'85 Westy-Wolf