I'm a little confused on the 103 build, did your dealer pull the engine, split the cases to install the 4 3/8" stroker crank and increased the bore to 3 7/8"? Did they swap the heads? does your heads have a Screamin Eagle tag on the right side? The reason I ask is HD did at one point make a Screamin Eagle 103 kit for the 88" Twin Cams, it made the 88 TC into the same 103 they used to use in the pre 2007 CVO bikes.
When you talked with Bob Wood I believe he was confused at which 103 you have, I'm betting he was thinking you have an 06 Dyna 07 and later Touring Twin Cam vs the 99 - 06 Touring Twin cam. Bob doesn't offer TW555 cams for your 05, the closest is the TW6.
You mention the engine doesn't like 2,000 rpm in 4th or 5th gear, 2k is too low of an RPM for a trike to be stooging around in 4th or 5th gear, your asking to shift the crank. I wouldn't run 4th or 5th until 2,500 RPM at the lowest.
I'm reluctant to offer cam advice not knowing just what you have in that engine. I can say you will have to pull the exhaust to change the cams.
Depending on how you want to go about a cam swap. If you stick with the stock push rods you will have to pull the gas tank, pull the rocker box tops off, remove the exhaust, remove the rocker supports, to remove the supports you will have to spin engine until the cylinder your removing the rocker support is on the heal of the cam lobe before you remove the rocker support. If you go to quick install adjustable push rods you can leave the tank on because you can spin the engine over until each cylinder is on the heal of the cam lobe and clip the push rod for that cylinder with bolt cutters. You want to make sure you have the service manual before you under take a cam swap.
If you haven't read it yet here is a thread on a cam swap for an 07 and later Twin Cam
http://www.triketalk.com/forum/threa...-and-up-Harley. Your 05 will be a touch different, the gas tank is a PIA to remove since you have a cross over line, your cam plate will be different and your exhaust will come off different.