Well if you stay in that 2,000-2,500 range you will almost have to get a 250 since 500's usually will run you more than that. A 250 is a great starter bike.
For gear you will need a minimum of helmet, jacket, gloves, and boots. Everyone doesn't wear pants but they are almost as important as all the other gear. You can get a good helmet for around $100-$200, a good jacket for $100-$130, gloves for anywhere from $20-$100. I personally wear a pair of goretex steel toe boots for riding but actual motorcycle boots may be more useful.
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