Let's talk... Ironhead Sportsters

JeffisOld said

PLEASE buy a 4stroke 250 dirt bike the same day.

Only ride the dirt bike for 6 months before you fire up the HD.

You cannot imagine the ways you can hurt yourself and I would like to read how much you enjoy riding later in the spring!

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Excellent advice! In fact, buy a dirt bike now and go "get your legs" - then sell it and buy your HD.. you're too big for a Sporty, period. I am 5'10", I have an 83 FXWG and you're probably too big for that too.. although it's been a great scoot for me and the Mrs and we have done some fairly long rides on it. I'm not going to try to point you in any direction - you have to decide what bike fits you and your needs.
I can tell that most older HD's are 100% CMV's (constant maintenance vehicles) - it goes with the territory.. it's all good. Anything pre-shovel is collectible (and the shovels are getting there) so IF you can find one you like that is for sale, it's probably gonna cost ya. Some real advice, just do it. And yes, take the riders course. I'm fairly arrogant and had my HD for better than 2 years before I took the course - rode on my permit - then decided I should get a license and took the course, I was surprised at what I learned.. stupid little **** that you would never even think of.