Sounds like a no-brainer for either the Davis Vue or VP2, depending on whether you find it important to be able to separate your anemometer and get it higher up in the air for more accurate data. I copied Greg's idea, my station is mounted on a mailbox post with a metal mast for the anemometer attached to it.
I'd second Chris' advice to site it with one side of the post facing due south (true, not magnetic) - it makes it easy to mount the ISS for maximum solar exposure, and also easier to point your anemometer's wind vane due north for accurate wind direction data.
Transmitting 500 feet from the ISS to your cabin shouldn't be a problem, so console placement should be a non-issue. You'll definitely want to buy the Weatherlink/data logger package so you can store and download your data. Make sure to read the manual and set your data storage intervals according to how often you get up there so you don't lose data.
As far as prices go, I bought my station and datalogger from Rainman Weather - in doing the math they had the best deal, but several other places were very competitive as well. Like you, I did a lot of homework before I purchased my station - the Davis systems definitely aren't cheap, but IMO it seems they're hard to beat for quality, accuracy and reliability.