Looking now and into the winter period is the best time to be looking and comparing used and nearly new prices; we did just that last winter.
You will find (as already mentioned here) that the volume of advertisments on Autotrader, here and on the VW commercials websites will increase significantly now we are in the autumn and approaching winter. Prices typically remain high but perhaps not as high as peak season due also to the additional vehicles available at this time of year.
My best advice; decide your base vehicle spec if you can. i.e. 140 or 180, manual, DSG or 4Motion. Makes your comparison for cost a lot easier, allowing you to decide which other options you can compromise on i.e. colour, options, accessories etc.
We watched used vehicle prices and specs last winter (as we werent ready to buy) and decided on our preferred spec/options, which in turn generated our preferred budget range to purchase this winter.
The Cali's are generally well looked after and from time to time older models come up for sale at low £30k prices. I think the cheapest I've ever seen was about £26k. Most used or nearly new vehicles tend to be £35k upwards depending on th eusual variants of age, mileage, spec, options etc.
I cant recommend hiring a vehicle enough though - contact Oli at BMVS for an excellent selection of vehicles and specs.
This was a massive bonus for us when we hired for a week. Primarily it allowed us to decide quite clearly what our preferred spec/options would be when we were finally ready to purchase.
Once you've hired, you also understand how everything works and - should you be planning on buying a used vehicle from a private seller - you will have a far greater understanding of what to look for in a second hand vehicle.
I viewed a private sellers vehicle last winter which was at a good price, I was seriously tempted to buy but in hindsight I'm glad I didnt. The Cali was probably fine, but it wasnt until we hired one that I then knew what I should have been looking at :crazy
As Californiaman has already mentioned, we recently ordered brand new as we found we could get a new vehicle for the same cost as a good spec used one. Whilst we had to compromise a little on specification of the new vehicle compared to a used one for the same cost, it was a no brainer for us to get a brand new unused fully warranted Cali.
Hope this helps and good luck with your search