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  1. They’re both usable options if the sizing and condition is good. Are you in the USA because prices are very high in USD. You can negotiate aggressively since it is winter and you are looking at fringe sizes these bikes are hard to sell right now. You can also join your local cycling club and send a message out to members that you are looking for a bike for a young athlete .

         

         
    The one I would prefer is the Specialized partially because it is newer. It also has better ride quality and that is very important for covering big miles when your are new. It has a relaxed fit ride position currently but it is possible to slam the stem and add clip on aero bars to make it competitive for decent level tri. The negatives are it is actually 2008 at newest with those shifters and more likely a 2007 with that paint job. It also has dirty bar tape so you are not buying it from someone who meticulously looks after their bikes which is ideal when dealing with 15+years old carbon. My expected price range for this would be more like 500-700      
         

    This era of Cannondale is famous for being stiff and also infamous for being stiff. It also only has 9 speed gearing so there is not many high quality new replacement parts, but plenty of parts bin stuff at least. It is still a good quality bike which can be used for ironmans. My price range for this would be more like 250-400

  2. Assuming the price is in USD i would buy something more recent. Usually in this period of the year there are less used bikes for sale (often overpriced), when the season start to get warmer you should see the number increase with more good deals, at least this is what i observed in my country.

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