No, you do NOT need to be a pro to own and ride a Harley. Almost the reverse is true. If you acquire one of these race bikes you might find your self going too fast in a very short length of time and distance to control the bike, especially being a novice...
However, NO bike is any better (or worse) than it's owner or handler...
HD's ARE more expensive. Parts cost more. The shop costs more. HD stands for Hundred Dollars, which is about the least amount of $$ you seem to be able to spend in their shop, for anything..
However, HD's keep their value better than most other makes, if you treat it right, and by right I mean the same care you should give ANY motorcycle. They are NOT more picky. If any bike(s) are more picky it's the ones with 4 or 6 carbs, duel over head cams and other high tech, high performance features with a gazillion adjustments..
HD's ARE low tech. Not too much can go wrong and then it's generally simple to figure out. Other than some of their new electronics and fuel injection systems, I doubt anyone could build a more simple engine.
If you can take the family lawn mower apart, and put it back together, and it runs, you can most likely work on many models of HD's. Not a whole lot of complex tools are needed either.
My bike is a 05 Heritage Softail bought Christmas of 04. It has almost 45,000 miles. The only work so far to it has been 2 flat tires, oil changes w/new oil filters, changed the plugs a couple times and simple adjustments as the bike "broke in" from being brand new.
Contrary to many opinions here, HD's are NOT slow or sluggish. Granted, they are NOT the fastest bike out there, and they are NOT made to be, however, by far, they are not the slowest either..! If you twist the wick (turn the throttle) hard on any HD, you might spin the bike out from under you because the rear tire broke loose from the pavement. As you wind the gear out and hit 2nd hard, you can break the tire loose again as well as feel the a$$ end fish-tail as it is doing this. Some times 3rd is the same way. By now only a few short seconds have passed but you have also passed the 80mph mark too and now beyond any legal speed limits for public roads anywhere in the USA. You are also going fast enuf in a standard city block to NOT stop in time for a car coming out of a drive way or a left turn in front of you. How much speed do you need..???
If you buy a "factory made chopper" you most likely will have good luck, however, if you buy some guys abortion HE called a custom chopper, you may have more nightmares than a whole city of Elm Streets and they all have Freddy's living on them.
Choppers are notoriously known as a fixer's bike. Many are built in the dude's garage and have so many "custom" modifications you may ride 1 or 2 months a year and the rest of the time trying to figure what the heII he did.. Don't do it unless you re-do the entire bike YOUR way so you understand the wiring, the mechanics, clutch, brakes.. etc...!
IF you should need part out on the road, during a "road trip".. will you find the parts you need..? Think about it.
No bike is a bad bike, but there are plenty of bad people who either bad mouth a bike or trash a bike THEN call it bad.
Good luck..
Bob - Tucson