The thing about answerers of these questions, is that those who ride american will answer 1 way, and those who ride japanese or don't ride & never have/never will - will answer the other
I've owned/ridden both
100% with no question, my advice says go for the Sportster
Price wise, you're right, they're about the same, but resale wise, the Harley will win, hands down. A used harley is always worth a good 20% more than a used japanese bike. So when it comes to pricing, the Harley wins
Looks wise, it's purely subjective there, beauty is in the eye of the beholder, nobody can argue that one, so your preference will be your preference. Though the tie-breaker here is that a harley has about a million different ways you can customise it with parts from harley or the aftermarket. You can easily make it unique and make it your own, a japanese bike is just a coocki cutter clone where they all look the same. Sure you can buy a few do-dads from honda, but it won't change its look much unless you go pretty drastic (and in the cases that guys work hard to make them look different, they look like a harley, so what's that say) Chalk another win for harley
Gauges, yep honda's are bigger. Honda wins that round
Shaft drive vs belt drive... again, it's subjective, purley an opinion thing. Both are maintenance free so they claim. Neither requiring routine maintenance or adjustment. A shaft drive can get out of adjustment, just like your rear diff in your pickup can start to howl so that one's bull, and a harley belt can have road debris wreck it, so it's not guaranteed to be for life. But in the end, a belt is cheaper, quicker, and easier to repair than a shaft drive. I'd call that a harley win.
Reliability. Again, purely subjective, and mostly a matter of opinion. Both are built by man, so both can fail. Both have decent warranty and both have decent history. My 2 cents says that back to that million ways to customize a harley, you will always find parts for your harley.... keep it 20 years and they'll still make em, the honda... i doubt it. Another win for the harley
And finally, the name/reputation.... no explanation needed, harley wins hands down.... why else does honda try their best to make their bikes look like harleys.
so you do the score and decide who wins, its your money, but i think harley has way more compelling reasons than the honda ever will - regardless of how many posts show up from posers who have never ridden a harley or an import for that matter for more than 10 miles in any 1 direction.
PS and the one who hated her sportster and traded for a buell and loves it... that's the stupidest thing in this whole thread... every buell is based off a sportster, do some homework