Since I don't have a road bike, I'll play along. $5k is a lot of spending power under my sleeves, BUT... I will still try to shop smart and not just blow it just because. Even though my ultimate drool right now is an Infinito, I also have to consider "other" bikes I've tested. I'm really satisfied with a lot of them, I only chose the Bianchi because there aren't many around where I live. So if I were to consider sales, there is this shop called Mike's Bikes that has some awesome sales like 30% off on bikes and accessories. Don't know how many times they have it in a year, but so far, they've had 2! So I'll probably go with one of their decent bikes like a C'Dale Synapse Carbon Rival, change the cassette to an 11-32, change the wheelset, a decent pedal, helmet, and shoes. Or be part of a South Bay cult and become one of a million owners of a Specialized road bike and get me a Roubaix for 30% off and do the same changes as above. I'd do Trek, Bianchi, or Scott as well if I find an LBS that offers 30% off sales like Mike's Bikes.
Anyway, it's all but a dream right now... $5k expenditure on a bike? Oh how I wish!