Solenoid is bad or shaft is broken.
These models had a weak starter clutch, specifically a poorly manufactured pressfit bearing in the assembly, you can get one for around 150-200 bucks. I've heard tell of a fix that involves using self tapping screws/rivets/small bolts etc but have not bothered to try this since it's more than worth my while to throw down $150 and save myself several hours of screwing around.
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SOURCE: 1999 ttr 250 starter motor is not engaging
I would guess it is the starer clutch, also called the one way clutch. I went on to www.bikebandit.com and looked up your bike and it has a nice exploded veiw of your starter clutch . I will try to put a direct link to it , hopefully it will take you to it. http://www.bikebandit.com/houseofmotorcycles/yamaha-motorcycle-tt250rl-1999/o/m7707
if not go put in your bike and look under starter clutch.
You will need a new starter rebuilt ect. to replace the one you currently have that is defective. you sound like you are spinning the starter motor but the starter bendix is no longer engaging the flexplate/flywheel on the engine.
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