Negotiation skills and buying a Used Car

I know this goes against common wisdom or whatever, but have you checked prices for new cars similar to what you are looking for used? I recently purchased a Subaru Impreza for one son, and I couldn’t find many used that weren’t close enough to the new price to make it worth purchasing used. I could have had CarMax ship a car to close by, but I would have had to pay hundreds of dollars (shipping from WA to east coast, for example).
Also, I know you didn’t ask about this topic, but you may want to check insurance rates before you buy. I bought my other son a used Scion TC last year (used CarMax, and it was easy, but certainly not the "best deal"around). I just assumed bc it looked similar to a Mazda 3, Honda Civic, etc. that insurance would be similar. The insurance on that car is really high. I think it has to do with it being a 2 door, and it’s considered sportier. On the other hand, when I called about insuring the New Subara, I learned that it would be $250 less per year than the cost of insuring the 5year old car he had before.
Good luck. Let us know how it turns out.