I say don't do it. Save yourself the anguish, buyer's remorse, and the pain and suffering of having it in the shop and bills thereof.
I love Harleys, but as a former Harley rider, I'd say why not try something similar but more reliable. How about a Kawasaki Vulcan 1700? They're very nice, powerful, reliable, less expensive and have that wonderful rumble. They also come in some great colors. If you really want the Harley, then get it, but check out some of the recent posts on this forum from others who have gone to Milwaukee with bad experiences. Another choice is to go with a real motorcycle, American style. Check out the Indians. Extremely reliable, silky smooth operation, great looks, and a lot of different color choices. Since you're looking at a Sporty, check out the Scout line.
I recently enjoyed Demo Days from my local HD dealer, and really really like the Road King. That Road King was very tempting, but then I thought about payments on a $23K bike and my past experiences with HD. Granted my experiences were back in the day with a 1950 Panhead, and a 1969 Sportster, but I can still taste the bitterness. I loved those bikes, and loved all the shenanigans that went along with them, but in the end, Metric bikes have provided a vastly different experience. My older Shadow 1100's are a bit more nimble, lighter, have plenty of power, and in the case of my Aero, have that wonderful Rumble. They haven't left me on the side of the road, they haven't emptied my wallet, and they're complimented as much as the Harleys.
One of my friends recently moved his Harley up to his weekend property, and took it in for service before the move. Service and whatever cost him over $2K, and his wife doesn't ride her Fat Boy any more. So, he's going to ride that one around town and discovered it too needed some service. That was over $1100. He said to me that his over 30 year relationship with Harley is over, and he's going to buy an Indian. Another argument is air cooling vs liquid cooling. I live in a very congested area, and when stuck in traffic (such as a recent gridlock in a tunnel that goes under SF Bay) my radiator fan kept going on. I remember riding in the desert with my old Sporty, and if the weather wasn't hot enough, the heat coming off the engine was very unpleasant.
I've tried to point out some valid considerations to talk you out of your pending foolishness. Have I succeeded?
Seriously, HD produces some beautiful bikes. Their designs are ancient, but improving with innovations like the Milwaukee 8 motor, much better brakes than in the past, oil coolers etc. The new suspension on the larger bikes like the Road King is wonderful. Still those improvements have been around on other brands for years....even decades, and at much lower cost.
By the way, that blue bike looks nifty.
Why is there never time to do it right, but always time to do it twice?
2000 Aero 1100
2002 Sabre 1100
1981 Virago 750
Last edited by w6wat; 07-16-2017 at 12:53 AM.