Early 1950's or late 40's 45WL would be a good old bike to have if you want a Harley. I would stay away from anything in the 1930's, trust me on this one, although they are the most beautiful (1933 is the best paint display on any Harley ever made) , they are hard to fix and parts (even after market) are expensive and hard to find. A lot of these bikes got scrapped in WW2 and Euros bought a lot of them too .Production #'s were low during the depression. The late 40's and early 50's WL's are beautiful and less complicated. All hand shifters are somewhat dangerous to ride .They have limited brakes and suspension so you have to ride them carefully ,and hopefully sober.Speed is not that important ,and you can get bucked off with only one hand on the bars. Just my 2 cents on the little I have learned. Good luck !!