I've got a new 160 GB classic, a 5th gen video with the Wolfson chip as my indestructible car beater, and two 5th gen nanos. I also have an iphone, and had an iPod touch for 2.5 years before selling it a few weeks ago due to non-use. Overall I've had ten ipods so I've got experience with many.
My suggestion? Get the new Classic. I'll break down pros and cons for quite a few models you're considering, at least the way I see them.
iPod touch Pros:
--Cool interface
--Apple's most adored iPod, and thus the one that will likely be most supported
--Application Store
iPod touch Cons:
--Touchscreen is a massive pain in the ass. You can switch tracks with a remote if your headphones have them, but I got really frustrated having to take it out of my pocket all the time. Mine was a first gen though, so no volume buttons on the side like the new ones. I hate my iPhone anyway though. I just flat out don't like touch screens. Like you said though, it will be docked so maybe this pocket issue wouldn't be a problem.
--Applications are a novelty that quickly wears off
--Designed to be more of a PDA than a dedicated music player
--Don't have the slickness and ease of the click wheel
--Dated interface--it hasn't changed since Apple intro'd the iPhone three years ago. Come on Apple, a little eye candy update wouldn't hurt once in three years.
iPod Classic Pros:
--Beautiful and elegant
--Massive battery life (huge for me, maybe not for you)
--Great sound quality IMO (I use treble booster on all my iPods)
--Huge storage...just in case
--Click wheel and all the ease of navigation that comes with it
--Great size and feel in your hand/pocket
--Fastest hard-drive based iPod I've used, and seriously gives flash-based iPods a run for their money, speedwise
--All bugs ironed out now that it hasn't changed much in three years
--It's designed to play music, and only music. A dedicated music player, plain and simple.
iPod Classic Cons:
--Hard-drive based. Be careful with it. The last of it's kind
--Outdated but proven hard-drive technology
--Likely to not be supported by Apple much longer
--Changed very little from 2007 to 2008, and from 2008 to 2009 literally NOTHING changed sans a growth of 40 GB, so in that sense it's dated and well in need of an update/redesign, if it lives past the coming of 128 GB flash chips
5th gen iPod nano Pros:
--Small
--Beautiful
--Flash-based
--Lots of features
--Hot item of the year, along with the touch and definitely going to be supported for a long time coming
--Click wheel and all that goes with it
5th gen iPod nano Cons:
--Perhaps too small for some
--Sound quality on the Classic I *believe* is superior
--Lots of features
--16 GB capacity cap
--Delicate finish
5th gen Video iPod Pros:
--All of the same as the Classic, but a possibly slightly better sound chip, though I HIGHLY doubt that even with amazing equipment you'd hear the difference. Apple doesn't sell millions of nanos and touches with crap sound quality--all iPods sound pretty smooth but it's true some say the 5th/5.5 gen video iPods have a warmer sound
--For being hard-drive based mine has taken massive beatings, extreme temperature changes left in the car in Minneapolis, and multiple hard drops and it still ticks flawlessly
5th gen Video iPod Cons:
--Old, perhaps not reliable and no longer supported
--Plastic screen is a bitch if you care what your ipod looks like
--Can no longer get refurbs from Apple--they would come from some random third party and there is no guarantee of a good product.
--Much weaker battery than the Classic (14 hours on a good day for these old 5th gens compared to an underrated 36 for the new Classics)
My opinion would be to get the Classic. My favorite by far and I can't recommend it enough. Big storage, big battery, proven design, elegant, dedicated to music, and feels good in the hand.
