In 8 years and 17000 miles (24500 miles on the bike now) ownership of my 883 sportster hugger, I think I am well qualified in giving my opinion.
In all this time, she has proved bulletproof, and the paint and general finish still looks like new.
She is still on the original battery from 1997, in the winter she starts up every 2 months without complaint, and get this when I originally got her, rode her for 5 months before laying her up for winter, the next spring at service time got a call from the dealer telling me there was no gearbox oil at all period! I probably ran her for 5 months without gearbox oil and guess what, that gearbox is still running sweet to this day! Try that on your Jap bike!
In 8 years of ownership, I only had 2 major problems, namely a battery terminal had corroded and perished, and this year the throttle cable snapped. Both wear and tear items and no big deal to sort out.
The handling is safe and secure, sure it's no sportsbike but then it's nowhere near as bad as non Harley people like to make out.
Brakes take some getting used to, especially 2 up, but you adjust to that fairly quickly.
But the best bit is that engine. It may not be that fast, but it wasn't designed to be.
To sum up, if you are thinking of buying a Sportster, go for it you will not regret it!