If you're itching for something like an Iron 883, then get yourself to a Harley dealer and check one out. Life's too short, and you can't count on doing something 5 years from now- you don't know what circumstances will be then.
I had to have a Harley back in the late 70s, so I understand. I got it out of my system and moved on, after having had a Kawasaki and a Triumph. People have lots of opinions about Harleys, so you'll hear it all. Frankly, it is whatever you want it to be. Dealer support is extensive, every part in available, and Sportsters are the easiest of the Harleys to ride, simply due to their small height and less weight.
There are a zillion low mile used Sportsters available from others who either decided they didn't really like it, or found it a gateway drug to bigger Harleys. You either get them or you don't. Since you're a Stella girl I think you 'get it'. You might find yourself loving an Iron 883.
Incidently, don't listen to those saying you can't ride any distances on a Sportster because they vibrate and fall apart- theirs a guy in ride reports that has toured all over the US and Latin America on one with his wife. Pretty Amazing...
2012 SYM HD200 Evo
1980 Vespa P200E