I'd go with the Heritage in a heartbeat. The used 18's out there are a completely different bike so I wouldn't compare them with the 17. The Heritage is not overly priced with the discount if you're in MI. It's a different riding bike than the Slim, no question but very versatile. It only takes about 5 minutes to take the bags and windshield off and you have a nice comfortable cruiser. Less if you get some quick release hardware. I have a 16 and went to it from a 14 Street Glide Special that I loved but was just too bulky for my. I'm 5'6" with a 28" inseam on a good day and it fit's me perfect.

And that color.......... is one of Harleys nicest combos ever! You're only $400 apart on the bike. Push a little and maybe you can close the gap. Or get the 5K service thrown in. Always things they can throw in when they need to make numbers.

 

Looks like your dealing with Battle Creek H-D, I've heard good things about them & always been treated well when I stop in....

I think they can do considerably better on the price, make 'em work hard for the sale ;-)

 

Based on the needs and wants you outlined, I would opt for the heritage. Especially for the color preference.

Yes buying from a dealer comes with a premium, but also comes a warranty and reconditioning.

I love to negotiate. But don't squeeze too hard that you focus on the deal and not the goods.

Enjoy!