A diagonal boom looks good to
A diagonal boom looks good to me because it parallels the seat back. To each their own. IMHO the aesthetics of the boom angle should be one of your last considerations.
I have a Silvio 2.0 with no chainstay extension (5'10", 45" x-seam, 175 lbs) and I have tons of room in the cockpit, maybe 7" of clearance from the center of the handlebars when I'm sitting back in the seat. Very easy to get in and out, or sit up straight in the seat. I imagine the 100mm chainstay extension would work fine if I wanted a more aerodynamic position.
Other factors I can think of: If you have shorter arms, you may want the handlebars farther back which will shrink the cockpit. I have relatively long arms. If you have a longer trunk, that will effectively shorten your reach since you are lying back. And, crank length will limit how far forward you can move the handlebars and still have knee clearance (once the pedals are moved as far as they can be for your x-seam).