Oh man,.... you are a glutton for punishment aren't you? This is the one place that all the Harley haters will come out with their mouths foaming to get the chance to indoctrinate a new rider. That being said: If you are an average sized guy the 883 iron or otherwise is a fine choice for a first bike,...but hey, any sportster is an acquired taste. Its not a good choice for a 6'5" 285 lb football player. Everyone I know that has a 883 loves it. Its quick and nimble in town and it is up to the task on any highway. its NOT an underpowered POS. -And its not a drag bike: its even tempered. The expert on this forum that actually rides an 883 is an Australian guy that, from what I gather can really put that thing to the test in the Australian landscape... he apparently gets good reliable service out of it. Nobody can refute the facts... your sportster will still be running when the imports are in the crusher. I admit I am not impartial,,, I'm HD all the way.
But what do I know, right? I've only been at this a couple of days.
(edit) Another poster recommended a 1200 sporty. Nothing wrong with that logic,... its a great bike. Very comfortable and gutsy. When you're ready to move up, thats a great place to land.