I am now the owner of this bike, and i have to be honest people did not take car of it after you... it leaks crazy amount of oil and has trouble starting.. but no worries i have just started rebuilding it today!!!

 

Where does it leak? Do you see the leak or does oil just go missing? Valve cover gaskets can leak pretty easily (read: incorrect torque on the cover bolts, or misaligned gasket, and then there are the half moons) and look like a lot of oil is getting out. If oil is just missing, check the coolant for oil and the oil for coolant. If you ride at high rpms some oil can be lost through the crankcase breather tube into the airbox, I've never lost enough to add oil though (BTW, my bike lives at 6-8500rpm on the road)
My bike doesn't like to start without choke, unless my valves are on the open side of spec. First time I shimmed just the exhaust and it started better, second time around I was able to shim them all to the open side of spec. They are all .05(IIRC) from the most open setting. Starts right up (@ 70ºF) and I can ride right off (with the occasional stumble).

 

Welcome to the gang, with a classic bike as well!!
Hope you get it sorted and shiny again.

 

Please share the story of how it came to be in your ownership. Last known home was Waukesha Wisconsin. Where are you located and who did you buy it from?

 

Well we took it apart and figured out the cylinder sleeve was as scored an scratched and im waiting to hear from billblue big bores to see how much is costs to get it re-sleeved. I will post some pictures soon. The oil was coming from the airbox breather hose and dripping intense amounts of oil and filling the airbox 1/4 the way full.. but for now to keep it on the road I am putting my buddies old 250s sleeve on! But I found it on craigslist in greenbay a month or so ago, it looked so cool i couldn't pass it up and got it for 3200$. Its now here with me in Waupaca, Wisconsin!!