I still have my 1988 Pinarello racing bike. When I was 17 (in 1988) it was a perfect fit. Of course I was younger, more flexible, and weighed a lot less than I do today. I still have it, and I'm considering rebuilding it for the umpteenth time if I can get the frozen handlebar stem out. I last resurrected it about eight years ago, and rode it for four or five years after that. In fact...I think that rebuild was my 30th birthday gift to myself! It certainly helped me get back into shape and drop a few pounds. Something about a fast bike just inspires me to ride hard, but I remember how weird it felt after riding my more upright commuter. The Pinarello is just a much more aggressive position that is harder on the arms, hands, wrists, neck, back, etc. I gradually got more used to it, but never found it as comfortable as it was when I was younger and in better shape. I called it fun for about two hours! For longer rides I wanted my more comfortable bike. The gears also make a difference. The Pinarello has a 42/53 chainring setup with a 13-21 cluster, so no slowly plodding up hills in a negative gear like I can do on my commuter.
As fun as it would be to ride this bike for another round, I'd rather get a more relaxed fast bike... and a slightly larger frame that will allow me to raise the bars closer to the saddle height... and maybe even a triple chainring. My commuter is very comfortable, but it's a touring bike with 700x37 tires. I can ride it pretty fast, but I'd still like a faster bike to ride sometimes.
Seeing the Pinarello in its current state (which is not road worthy) makes me feel old, but you know what makes me feel really old? The fact that covet my wife's mixte upright comfort cruiser with the swept back albatross bars! Not only is it extremely comfortable, but it's just a fun bike to ride... but at the opposite end of the spectrum from my old Pinarello. Seriously though... after 25 years of cycling I'm just glad I can still get excited about it.
My ideal next road bike would be fast, comfortable, lugged steel... reminiscent of my old Pinarello but slightly less aggressive and a bit more upright (actually more reminiscent of the Trek sport-touring bike I had in the mid-80s). A custom Rivendell perhaps! I'll tell my wife that is what I want for my 40th birthday, so she better start saving her money
Sean
PS: One note on making your Bianchi more comfortable... and I'm considering this for my Pinarello: Replace the existing stem with a Nitto Technomic. The Nitto's have super-long quills so you can raise the bars higher than with most stems.