Crispy - great post! I wish everyone would present that kind of information to get started.
I think you would do well to get started with a lower to mid priced Gyuto to get a basis for opinion and preferences, as you stated. That being said, the Kohetsu, which I consider mid-level priced, is so darn good for the money, it might just be a one and done Gyuto purchase for you. Meaning that you won't get a ton of performance gains moving up the food chain from there.
I really wouldn't worry about the clad vs. mono steel feel at this point. Most people probably won't notice much of a difference. Out of those that do, even fewer likely consider it a major factor in the experience. Are you one of those people? If you really want to know, then at a later date you could get a mono steel blade and discover if you feel the difference or not.
The Konosuke is a great knife, but pretty spendy if you're not sure about preferences yet IMO.
Mark just release a new knife today that might be of interest. The Goko 240 Damascus Gyuto: http://www.chefknivestogo.com/goko.html
. It's brand new, so no feedback yet, but it looks like a promising performer, especially at the 30% discount Mark's offering.
The Tojjiro is a great bread knife. That or the Richmond Artifex bread knife would be my picks: http://www.chefknivestogo.com/riarbrkn27.html
I'd maybe wait on a petty until you've had some hands on w/a Gyuto (or 2).
On the Honesuki, that's a very task specific knife and it's not really intended for rough duty. If you break down a lot of whole poultry/birds, then it might be worth doing. Also, many Honesuki's are right handed single bevel blades. Keep that in mind if you're a lefty.