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Good advice above from good people. I will add the following for your purchase of long time rider....
Welcome from Spartan Country, Michigan! I tell a lot of new comers to the forum to get: Factory Service manual and the Parts manual. Get a three ring binder and record all your maintenance, repairs, accessories, etc. This will be a great reminder of what was done when. And great material to pass along to the new owner should you sell and upgrade. Also know how large your fuel tank is, and record your fuel usage. I have an app called Simply Auto that I record all my fuel used. I use the odometer and use the fuel gage as reference only. I reset the odometer to zero on fill ups, and I know I can safely get 200 miles on a tank on around town riding. Good Luck!!
I agree with you on the points you made in the 2nd and 3rd paragraphs, but not in the first paragraph. I think most riders have some kind of idea in mind of what they want to ride(general class of bikes). They may change that idea later after they already started riding and find out they prefer a different style, like ADV for instance. By virtue of him coming to a Harley Davidson Forum, I think he already has a cruiser in mind, since Harley doesn't make sport bikes or ADV bikes at this time.
I didn't mention anything about sport bikes or ADVs. My thoughts were more about short or long trips, taking a passenger or not. You can't know till you start riding. I've seen a number of people buy a Sportster or a Slim or similar and then find their friends want to go on a week's trip to the mountains and they have a peanut tank or nowhere to put bags, or how to take the wife but the bike is set up solo. Also friends that buy an Ultra and just do 20 miles on a Sunday for breakfast and wish their bike wasn't so heavy.
I would recommend that you go around to as many dealerships as you can and throw a leg over as many bikes as you can. See what feels comfortable for a guy your size.
I'm a 6'0" old fat guy who isn't that limber. I barely fit comfortably on a Street 750 with the tall boy seat. At 6'6" I don't see any of the Street series of bikes being a good fit for you.
Your first bike is highly likely to get dropped a time or two. That could be due to an unexpected engine stall or simply forgetting to put down the kickstand when you walk away from the bike. Try to avoid a bike with a lot of fairings, hard cases, or other things that will break when the bike hits the ground. Look for a bike that has engine guards and leather or textile saddle bags that will absorb a shock and protect the actual bike.
Buying a used first bike will hurt a lot less the first time you drop it. My first bike was purchased new because I didn't know anything about motorcycles and didn't know anybody who did. If you have somebody in your circle of friends who can probably spot a bad used bike, take them with you and get a used bike. Just don't blame them if problems turn up later.
I didn't mention anything about sport bikes or ADVs. My thoughts were more about short or long trips, taking a passenger or not. You can't know till you start riding. I've seen a number of people buy a Sportster or a Slim or similar and then find their friends want to go on a week's trip to the mountains and they have a peanut tank or nowhere to put bags, or how to take the wife but the bike is set up solo. Also friends that buy an Ultra and just do 20 miles on a Sunday for breakfast and wish their bike wasn't so heavy.
7 Surprising Harley-Davidson Products that Are Not Motorcycles
Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.
Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?
Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.
Engraved Rebellion: Inside Bundnerbike's Glam Rock II
Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.
Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.