Carb is more friendly.
Honestly i have a '12 and i never use 6th gear. However i would pick up a 09 just because the newer the more refined and bugs are out of it. Buttttt..... That being said i wouldnt mind a carbed bike. Either way just look around and find a cherry well maintained bike and it doesn't matter.

 

Yeah the only reason I can see for a carb version is easy to work with if broke on the side of the road(typical old skool Harley) and the sound. I figure efi can't be that bad if you get the right tuner and software. that and can't you use a good tuner to get a better sound. like a thundermax or something.

 

02 carb, has the best crank & timkin bearings.

 

No problems with my '07.

 

"they sound like crap" explain please............ mine sounds pretty damn good.

 

Carb does have a lower idle and slightly better sound, but you can get real close with some cams and head work on an EFI. Never had issues with my EFI, so for the start and go reliability I would go EFI again if I had the choice.

Watch out for the 07 (?), I think that was the year of the weird axle size. Makes it a bit harder to find wheels.

I can't tell you what to get, but I can say I'm happy with my 05 88" 5 speed. I've run 80-90 for extended periods of time out west and had no problems at all. IMO, a good 88" with some cams and headwork will whoop *** on a stock 96 all day long. You can get them a bit cheaper and throw a little into the engine.

Cam chain tensioners have been an issue (IIRC, pre 06?), though I'm not sure it's as big a problem as everyone thinks. Sure, there are hundreds of guys on the internet who have had them fail, but Harley sold hundreds of thousands of bikes. Plus, it's a plastic shoe that a chain slides over at high speeds, heat, and tension. Hmmmmm, I wonder if that's gonna wear out that plastic piece? It is a wear item and should be checked regularly. Some need changed at 15k, mine are at 50k and still look new. Depends how smooth a chain you get.

Good luck with the purchase, post up some pics in the train thread when you get one!

 

hell yeah man, will do. loving them white walls.

 

I wanted a Night Train and had to make basically the same decision. Eventually I came across one at what I thought was a very good price, so I jumped.
Ended up with an 03 (100 year anniversary) with the 88b motor and carb. I love it!
I came from a 2010 Harley-Davidson Iron XL883N that was EFI. The EFI is stupid easy, you don't have to tinker with anything. There's not even a reserve for the gas. No choke to play with either. Tuners and things of that nature can cost you though.
But I love the old school of the carb. It sounds great, especially when you push the choke in and get that slow idle and the trademark po-ta-to po-ta-to po-ta-to
I feel a little more connected with my bike now. However I do feel for my neighbors at 5:50 AM while I'm warming her up.

 

Just look around and find one you like regardless of the year. I love mine!

 

I love the sound of a 88 with a carb and a nice cam!