Awesome. Test out the difference in the bikes. I have a Cannondale Synapse 5 105 alum myself. I love it and it has eyelets for fenders, not for a rack. Are you planning on commuting to work? Are you planning on riding in bad weather? Some bikes struggle with 28mm tires due to brake clearance. If you do decide to go with 28 have the shop you are buying them from make any brake adjustments for you.

Try the "endurance" bikes and try the ones used for racing. You will feel the difference immediately, but it'll help you decide what you like and what you don't. The geometry of different models make every brand feel different, along with the type of tubing and wheels.

You can probably wait on shoes and pedals. Keep money allocated for them, but get used to riding a road bike for a bit (a couple of months).