Well I did exactly what the OP suggested. I was in a Citroen AX 1.0 E(conomy) and was looking for something a bit bigger. I found a 146 at my local garage and absolutely loved it. When I bought it asked the salesman if he thought the insurance might go up on it - he laughed! - then I did when I saw what it was going to cost me! You know I'd probably have another now. Then I had a 156 2.0 Turismo, a 156 1.8 Lusso, a 147 2.0 Lusso, a 159 1.9 Turismo, a 147 1.6 Lusso, a 159 1.9JTDm Lusso and then an Audi A3 - shock horror! I fell out of love with Alfa - or more specifically with the dealer (They claimed the connector for the anti-lock brakes 'fell out', Alfa wouldn't confirm that it wouldn't happen again and they were right - it did 30 minutes after I put the phone down!) however it caused me so much (back) pain that I sold it within five months and now I'm in a GT blackline. And it feels good.
All this time my wife had her first new car - it was a toss up between a 147 and a Honda Jazz, the head said Jazz and she bought it and hated it. Within 12 months she was in a 147 and now she's in a Mito.
So yes definitely gotten myself - and others - into something way more than I expected.
146 1.6TS, 156 2.0TS, 156 1.8TS, 147 1.6TS, 147 2.0TS, 159 1.9JTS, 147 1.6TS, 159 1.9JTDm, Mito 1.4, GT, Giulietta 2.0JTDm, Giulietta 1.4tb, Giulietta 1.6JTDm........