I recently got back into riding with a 2020 Street Bob and am thinking I would like to add a vintage Harley to compliment the new bike. In this I find myself drawn to early Sportsters for some reason, though I have never really cared for them before. I like the looks, they are relatively affordable and they are simply classic.

Here is a '58 I am considering. The owner is asking $6500 and I am wondering if this is a decent price. I haven't seen the bike but it looks gorgeous from here.



1958 Sportster

Failing that, I will take anything pre-1980. I don't know much, but I do know that the AMF years start in 1969 and they are supposed to be inferior quality after that, but I wonder how relative that is after all this time.

So, any tips on buying myself a vintage Sportster?

 

I’ve always wanted a Then Came Bronson bike. 1969 Sportster

https://www.motorcyclistonline.com/1...-bronson-bike/

 

Eye candy or a rider? If a rider, you should know some mechanical things. Sure you can find a old school mechanic to work on it but most Harley Dealerships people would run out the back door.

 

all pre 1975 Sportsters have the shifter on the right and brake on the left ... just something to remember when riding

 

While I would really love to put it in my living room as art work, there is no way in hell I could resist riding that.

 

I never got use to the brake and shifter being reverse, so I had to stay away from Sportster back then. Still they ware a great looking bike.

 

better to buy one in great shape like the one u posted then buying a cheaper basket case
as mentioned the right hand shift is a deal breaker for me. if i only had one bike with right hand shift maybe but wouldnt like having left hand shift bikes at the same time and having to jump on the righty. do u want kick start or electric start

yes they had right hand shift till 74-75 and those were AMF's (69-81) i would take an AMF as long as it was clean
much more enjoyable working on a nice clean cycle that 58 is nice

 

The XLCH shown will be a bear to start. Unless you live on a high hill. I would get an XLH with electric start.

If you really want an XLCH, try to find one with manual spark advance system. They are a little easier to start. Some of the later XLCH bikes have a battery system which will help with starting.