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A bagger (depending on you and your passenger's size, and luggage requirements) probably makes more sense than trying to turn a dyna into a bagger (which just makes it look ugly)....might as well go straight to fully functional ugly, and buy a bagger to begin with.
My wife got a Dyna first and we ended up trading it in after less than a year for a Softail Deluxe. I have an Ultra and we do a lot of 200-300 mile rides. She is much more comfortable and can do longer rides on the Deluxe. It doesn't wear her out as fast. BTW, I started riding an Ultra after not riding for 35 years and it wasn't too much to start again on.
If you are going to do a lot of longer overnight rides, get a Road King or Ultra.
Dynas are great bikes...I love mine. BUT, by the time you add bags, windshield, a back rest for your better half, etc., you may as well get a Heritage. It's ready to go right off the showroom floor.
JMHO of course.
Well, yes and no. I have the HD quick-disconnect windshield on mine. And I have Ghost Brackets for the bags, and the HD quick-disconnect rack and backrest, and a removable pillion. So I can switch from a "mini-bagger" to a "solo bar hopper" in about five minutes. You can't do that with a Heritage. ... Of course, now that I have this weird thing bolted to the bike, it takes a few minutes longer to make the conversion....
We've ridden two-up plenty. And I do think the Dyna is a fine bike for 200-300 mile rides, two-up or otherwise. I think it boils down more to aesthetics. I could buy anything in the line-up, but I much prefer the look and feel of the Dyna. And I can make it work for about anything I do. Buy what you like.
As for the dealer, I wouldn't necessarily be so cynical. As someone else suggested, he may be pushing the Dyna because he genuinely believes it may be the best choice for you. And he may be right...
So far the advice here is solid but the other issue here is, are daytrips the only thing you are going to be doing? If so then the touring bikes would be nice and the road king would be about the right size electra glide may be overkill for just that trip. If your going to be using it around town, back and forth to work, bar hopper the king would be a handful, I would look at the softail and dyna. And that is the choice between style and riding style.
I had a Dyna for 18 moths, loved it, Did 500 miles two up at one go and had no problems. Borrowed a Fat Boy whilst the Dyna was in for a service and entered a whole new comfortable world. Smoother, nicer to ride two up, wife loved the bike. Tried the RK, to much baggage, I like the stripped down look, so it was the Fatty for me. I can put wind shilds on, Paniers, soft luggage if I want or just go off with a day bag. I think I'v got the best of both worlds, best advice I acn give, is to go and try the bikes and discover the best one for you.
The best bike H.D. makes is the Dyna, But not for long trips. I have been a mechanic for over 45 years and the is set up right, you can work on it, with out taking a bunch of junk off to do any thing. from a service stand point it is the best.
Like Ozoneman, I had not rode in close to 30 years and went straight to the Ultra. Found a sweet deal on Craiglist that included many extras that would have cost thousands off the shelf. There are tons of deals out there unless you are hung up on buying new. Don't rush and try them all before you buy. Don't let the dealer influence your decision one way or another. Good Luck!
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