You're not getting a Harley for that. Love them or hate them, they hold value better than metric bikes do.
And honestly, I prefer a Harley. They're not fast, they're loud, and contrary to popular belief, they don't fucking leak oil, post Evolution.
Low speed maneuverability is fun once you get the hang of it, and once you learn how to grind the footboards into the road, you can hang with most sport bike riders out there today. Most of those guys can go fast in a straight line, but they choke when the road makes a bend.
And trust me, a Milwaukee vibrator will get you more tail than any other bike out there.