You seem to have more than proven that you love cycling. You've done some serious riding -- on a hybrid. So I don't think you need to worry about whether you'll "stick with it." And I know you say going faster isn't important to you, but I think with a road bike you'll discover a new love for speed.

I don't get into mechanicals, either, so I totally understand where you're coming from on that end.

You say you could afford to spend $3,000, so I say look in the $2,000-$2,500 range and leave $500 to get some nice pedals, shoes and whatever other accessories you need. Make sure the gearing you get will be suitable for your trip in Italy (don't know how much steep climbing you're going to have to do). You don't have to be a gearhead to do this -- just tell the shop what kind of riding you're going to do.

You have the luxury of getting a nice bike, and I don't think you should waste money buying an entry-level road bike that you're just going to want to replace in 6 months or a year.