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I haven't regretted it yet. I think the Street Glide is the perfect bike to get your feet wet with a touring rig. It does both so well. I had a Street Glide and I thought I needed a bar hopper, so I built a custom bobber. Started with a Cross Bones and added a 113" motor, bobber fender/seat kit, ape hangars, etc. Was a sweet bike and really comfortable too. Problem is, I loved my Street Glide so much, I never really rode the bobber, so I sold and and bought a whole house generator and haven't looked back. I'm a touring bike guy for life now. (46 years old) Even stepped up to a limited recently.
I had my SG for two years but didn't enjoy it around town so I bought my Softail SS for around town and runs under 200 miles. I find myself gravitating to the Softail more than the SG but try to divide my time between the two (don't want one to get jealous).
If you have the space and funds, I'd recommend having two.
I bought my Electra Glide with the intention of using it and the Softail equally.. Didn't work that way. I ride the touring bike all the time and the Softail doesn't leave the garage. It's going up for sale. I swore I'd never sell that bike, but the Electra has been ridden thousands of miles compared to 10's of miles on the Softail. I didn't think I'd ever find anything I liked as much as that bike until I made the move to a touring bike. Having the space to carry everything I need with me at all times makes it a very useful and fun vehicle and I find that I'm riding a lot more now because of that.
After you buy one you'll be asking yourself why you didn't do it sooner and not only that but I'll bet you see that you do not ride the other bike at all or very little if you keep them both.
You'd be wise to trade it in and call it a day.
Trust me.
The only regret I have is not doing it sooner. I would definitely rent a couple and put some miles them. It ain't cheap, but neither is buyer's remorse if you make the wrong choice. You can also keep your ears open for Harley's "demo days". It's a free way to ride pretty much the entire fleet.
wow, another sporty to SG here.. i don't regret it at all. i wish i had it still just for around town and work and back but my SG does that just fine as well while blasting tunes and holding all my crap.
I had a Dyna before I got my limited don't miss it.The only thing you'll miss about the Sportster is how much easier it is to clean and maintain.I ride the Limited damn near every day year round all the storage makes it much more useful than any other bike I've ever owned.I do find myself lusting for something like a KLR though, I'd love to have something I could ride hard and put away wet as opposed to the constant cleaning and polishing of my Limited.
I'm all about comfort. On long stretches, I love putting my feet up, putting the seat back a bit, putting cruise control on and turning up the sound system. I'm a pack rat so I like carry stuff with me. Even if I go to the grocery store, I'll throw on my tour pak to carry groceries. There's no way I'd ride anything other than a touring bike.
Actually, when I see guys with those small bikes, I wonder how comfortable they are.
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