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1) For comfort the touring line is hands down the best. As for the exact model, it really is up to your preferences. However, the roadking is a bike you would have the ability to remove the windshield if you decided you wanted some air and it's one of the more reasonably priced entry level touring.
[/align]2) Once you jump up into the bigger bikes they all have about the same seat of your pants feeling, until modifications are completed.A stage 1 upgrade is resonable in price and will probably give you more than enough torque/horsepower to start out with. Quite frankly the Stage 1 in my opinion should be a stock item.
3) The Ultra Classic is the best for wind and comfort when money is no concern. The Street Glide and Road Glide are good alternatives. Then you step down into the classic windshields which can be installed on all the other models.
4) Well I own a deuce for my first bike, because of the feeling of being in the bike versus on the bike when riding. Additionally I purchased used and it already had many of the upgrades which I wanted. When I was looking though I would have been equally happy with a Fatboy or Springer. One thing I don't like about the deuce is it is usually on the fits allsoftails (except the deuce) list for accessories. [/align]
5) I would not order a kit, get exactly the paint job you want at a good custom painter for half the price. Try these guys http://www.attitudecustompainting.com/
I bought a Dyna Superglide.
The reasons:
- wasn't comfortable on a Sportster.
- I mainly ride in Milano, a city with lots of tight bends that can be difficult to negotiate with a longer wheelbase bike.
- Like less rake in the fork for the same reasons.
- had more torque
- costed a lot less than most softails.
For your necessities I think that a Superglide with windishield would be very good. It has the power, the torque, is comfortable.
As an alternative, I'd considera a Road King, but it's more expensive.
I own a Dyna (WideGlide) so I can say this - go for a Heritage Softail. (have that too)
The Heritage offers the comfort and highway stability, wind protection and storage, but is easily adaptable in that you can strip it down in minutes if you want to just custom cruise. The bike is fast, yet easy to maneuver in heavy traffic. If I could only have one, it would be the Heritage, hands down.
For two up I would not go with a Dyna. I would stick with a Softail (Heritage Classic w/detatchable windshield) or a Road King. Dynas are nice, and you can attach a windshield, but you won't be really comfy riding a passenger for long. JMO.
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