Besides the can chain tensioner there are fewer issues with the 88/5 speed than the post '07s. I never rode one, but all kinds of threads about heat, bad compensators, EITMS, limp mode, not liking throttle by wire.
So every year has it's issues. Find a bike you like and chances are it will be fine. Most people like whatever year they own.

 

I would look around a little more my local dealer had a 04 hertiage with 18 k for 8999.99
I have seen quite a few like that, but must be patient.

 

I would go to Columbia TN to the Harley dealer there. They have the best deals and prices in my opinion. Google them and look at there used bikes. I have bought two bikes from them and am very happy. It is worth the drive.

 

Nice bike. Yull be happy with that. Good color.

 

Great looking bike, enjoy!

BTW, don't let people scare you about cam tensioner. Just consider it a part of the maintenance. My '02 Road King had 50k miles on it with one cam tensioner change when I changed the cams. It isn't a big deal.

You can always update the cam plate or go with gear drive cams.

 

Congrats the Heritage is a great bike.