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Advice on Buying a Telescope

My grandson will be 14 on Christmas Day. They live on a lake in Texas. I would like to give him a telescope and tripod for his Christmas and birthday presents. I don't want to buy a kiddie telescope because I want him to be able to use this for many years. Yet the little reading I have done indicates that using a telescope can be challenging. Does anyone here know about telescopes? This would become a family gift, with everyone using it, and his parents certainly would help him. What should I look for or avoid in making a purchase of around $200 or so.

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