go with a yz or cr.
125/250...doesn't really matter. Both are reliable as long as you care for them. I have a fully built 2001 yz 125. Very happy with it, no problems at all.

 

What do you need to check out on a dirtbike before you buy it.

What questions to ask, I'm going to be on the market soon but I don't know much at all about them.

 

my suggestion's: check to see when the top end was replaced and ask to see receipts, check the tires, chain/sprockets. Start it up and make sure you don't here any knocking noise when the bike is idling down. Check the air filter, check the oil to make sure it's clean. Or just buy a new bike and make your life much more easier.

 

I like to make it hard on myself.

I don't want to pay the premium for new when I don't expect to stay with them for too long.

I will ride dirt for ~ year to have fun and get some skills that would be more difficult to develop on the street.

Then try my hand at the street.

 

Derek get a 4wheeler and keep it at my house i swear i wont ride it

 

BOB you probably have the best plan, better to explore a dirtbikes skills offroad where the consequences are not as high.