Here is an 86 Softail I had. ( sold it couple years ago).
I think that was the first year. They are easy enough to wrench on but not my favorite handling bike. Of course mine was 15 years old when I got it but the shocks in the rear had almost no travel and the front forks were marginal even after I re-built them.
They are low and bottom heavy which makes for a solid feel until your in the twisties.
I agree with BadgerOctane that CraigsList is a good place to watch. I also like to go to swaps and events and keep an eye out in the parking lot for bikes that are riden. People are usually ready to sell and they're in running/riding condition.
When I had mine I was wanting a 93-newer but couldn't find one. I can't remember why now, (I know the rear shocks are different) but you may ask around more on the differences. Good luck and enjoy!