My last two service visits to Maranello I had 323 and a 328 as loaners so its been useful to live with the cars for a day or two.
The 323 was a fine car and would be a more than suitable DD. It was sluggish to get moving but once you're cruising the hwy you're fine. The 328 had lots more umph, as you'd expect, plus you get xenons, better stereo and few other little things.
It simply going to come down to money. If I can get into a CPO 328 within 1-2K of what I'd pay for a 323 anyway then its worth it. If the difference starts creeping into the 3-4K range then it not worthwhile, to me.
I think I said in the OP...I have a family, properties, investments, main family car (X3), blah blah...oh ya then comes my DD. If it was just me, I'd be in a M3 or something no problem. Logic says, I can drive a brand new Civic for < 20K but I just can't do.
Life is like a sh!t sandwich...the more bread you've got, the less sh!t you have to eat.