2014 Limited
Take a rider course you'll be amazed at what you will learn. Buy the limited and TAKE IT EASY for the first season. Concentrate on your skills, head turn, friction zone, counter steer, etc. and wait as long as possible before adding a passenger. That extra weight and higher center of gravity changes the whole dynamic of the way the bike handles. Good luck and welcome.
A couple other suggestions that I would throw your way is find a bare bones used 500 or 750cc street bike to get some time maneuvering and operating a street bike. You should be able to pick one up for $3-$4k and after a couple months, get your money back. This way when you lay it over, (which you will at some time) you can easily pick it up and brush it off for a few dollars.
If you plan to do some group riding, start with 3-4 friends to learn staggered formations, hand signals, how to deal with road hazards, etc. I was on a Christmas toy run with a first time group riding rider and she were terrified. (So were those around her)
You might take the Advanced safety course as well with this lighter bike. I started back after 16 year hiatus from riding and I am glad I didn't jump at a $30k bike as my start point. It would have been an expensive lesson(s).

After you have some miles under your belt, (the more the better) you can then add on your most precious cargo and enjoy many miles together. Baby steps can be your best teacher.
If you're the type who digests information well by reading, I can tell you I found "Maximum Control: Mastering Your Heavyweight Bike" by Pat Hann informative and pertinent to the riding of big cruisers. Most "how to" books these days are more aligned to the sport bike rider. This one isn't.
The Best of Harley-Davidson for Lifelong Riders
Everyone's cautions are well enough founded but there's no point in making this out to be more than it is. You are a mature enough rider to be able to stay within your comfort zone while riding & cornering and you can resist the temptation to keep up with a group for the sake of misplaced pride. Remember the Rule to "Ride Your Own Bike". Do that, take a course and you'll be safe as anyone else. Guys who have been riding 80 years can corner faster than you (and me) but the prize money ain't that great
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You already know how to ride. Take an MSF course. Ride within your limits. You'll be fine. You're much better off than the dude that buys a Harley at age 49 that has NEVER ridden anything before, doesn't take a course, doesn't know what the front brake is for, doesn't know about downshifting, counter steering, etc. (there are several in my HOG - they are scary to ride with).
I would suggest that you rent a Limited first to make sure it's the bike you want to learn how to ride. They are a different beast than a dirt bike.








