Depends on if you are leaving it bone stock or you are going to add stuff to it Bars, wheels, etc...In my honest opinion not having fuel injection is not a deal breaker in fact I prefer my 05 carbed fatboy over my old 2012 103 street glide. I can tell you one thing when I pull up to a spot and everyone has there fuel injected bikes running and mine pulls up with the "potato potato" you can see smiles...look around for a clean older bike for around 8-10,000.00 you can find them. I guess it depends on what part of the country your from because the night train has always been a sought after bike on the west coast..bottom line don't let the year of the bike steer you away from it.

 

Don't know what you mechanical ability or experience is. As others have stated, Heritage is just what is implies, there will be a few upgrades but the overall look will be hard to sort between years. I just picked up a 96 FLSTN for less than many have in add-ons. I put 1K into replacing crusty parts and some mechanical issues.
You can't find them every day, but they are out there. I'm out of pocket a little more than the interest on new one financed for 5 years and at any time I can turn it for 2-3K profit.
Bottom line - do you need a warranty, just like new, more interested in saving money. Only you can decide.
Night Rod to Heritage - two completely different world.

 

A lot of good Heritage's out there for reasonable prices. It's one of the Harley models that's best purchased used. I wouldn't look for anything older than on '07 due to the improved cam tensioners and 6 speed tranny.

 

No need to spend more money on a 07 + bike!!! Trust me I have ridden them all and I said it before and I will say it again 3/4 of riders will NEVER notice the difference between a 88 and a 96..DON'T DRINK THE KOOLAIDE!! Look back in the 70's guys used to ride cross country on a rigid and their chicks would ride on the fender with a horse blanket as the seat, I'm guessing most of your riding will be in town or within a 100 mile radius? If so the added cost of a 07 + bike doesn't make much sense to me if you happen to go on a long trip go rent a touring bike..

 

A new black heritage is 18,300. and that is with abs standard!!!! The 2012 did not have abs standard and that price on the bike was I think 700 less. So to ask for 16 or 17 for a 2012 seems high to me. A new heritage is 18300 black 18700 color and 19 for two tone. you should be able to get a new 2014 for a grand off msrp. just my 2cts swifty

 

One thing to decide on before looking....do you want ABS or not?

They started offering it as an option in 2011 or 2012.

Also, in one of those two years is when they went to the CanBus electrical system.

I picked up a slightly used 2012 (3400 miles) Heritage w/ ABS in early 2013. PO had put some extras on it, and it was still under factory warranty. I paid around 14k for it. But, that was after a lot of shopping and negotiating.

 

The 1999 have the Evo engines. 2000-2015 are twin cams and are pretty much the same except for engine and tranny size. Rest is extras. I wouldn't worry about the cam tensioners on the 2000-2006 bikes. If you can work on a bike you can change these out for as little as a $100 or as much as $1000.

I don't know what they are offering as a trade in on your V-rod but you can pick up an older, low miles heritage for easily less than $9000.

 

Your post caught my attention because I have a Heritage and was thinking of trying to trade it for a Night Rod! It is a 2001 with a 95" big bore kit, gear drive cams and is very fun to ride. Just thinking of trying something different so I understand your dilemma. Love my SG but riding different type bikes is fun too. Good luck with whatever direction you go.

 

The difference bewteen an 88 and 96 may be negligible, but there IS a difference between the 5 speed vs. 6 speed.

I'm pushing 60. I appreciate the supposed "good ole days." But you can have your EVO's, carbs, and 5 speeds, or what have you. For me, I'm living the dream with today's ECU's, ABS, cruise, 6 speeds, and such. Make my Koolaide grape, please!

 

Lol...ok no problem one grape coming up. Just curious what benefit do you see a 6 speed over a 5? Gas mileage??