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Helmets: The newer helmets not only fit better, they are lighter, more ventilated, have wicking pads and I suspect slightly stronger (bonding technology is better than it was in the early 90's). But they are way more expensive! I remember trying on the Giro Boreas and eventually breaking down and buying it. Now I let my friends with old helmets try it on just to see the "wow" expression on their face. The Loc Roc thing helps them fit better than any old helmet using pads could. They even get around the old rule of helmet shape (round or oval) being crucial to fit (Bell is round, most others are oval). Road bikes: Get a triple if you need it. Get fitted properly. Go to a bike shop that will spend time with you doing that. Then it won't hurt. That's probably more important than which bike you get. Try aero bars. Finally, if you ride around the city and through parks and on bike paths, try a hybrid bike.