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Definitely take a riders course. The Motorcycle Safety Foundation (MSF) is a good one. Don't make the mistake that a lot of people do. When you finish the course and get your license you are not a proficient motorcyclist. You have been nothing more than taught the basics and it will require you to practice, practice and practice the rest of your riding life. It's a wonderful sport but you have to be on your toes all the time. You need to always be alert. They don't teach it any more but when I taught MSF we used the word SIPDE.
S - Scan for any possible threat to your safety
I - Identify those things that might cause you a problem.
P - Predict what that person/vehicle might do.
D - Decide what to do if they do as you suspect.
E - Execute when they do.
A 250cc is a good starter bike and yes, definitely buy used. You will drop your bike in the beginning and you don't want to do that to a new shinny bike. The only negative thought I have about a 250 is that many beginners tire of that small of a bike pretty quickly. It will only after you've been riding for a while that you will begin to develop different likes and dislikes about different types of bikes. It takes time to really decide what bike you want "it" to be.
Good luck.
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