So I have a crafty friend who has built maybe 5-7 lugged frames over the past few years. He currently resides in Boston and hangs out with some pro frame builders in their shop and uses their tools. I have chatted with him a bit and he has offered to build me a frame at about cost. In addition, I bought a tube set enough to build a frame for about $40, so I thought that this might be a great opportunity to have something unique that is more tailored to me. Looking for a lugged sport touring type bike.
I am going to a physical therapist that has fit me to my litespeed in the past. He has one of those Calfee custom sizers. This will be nice because it will take some of the guesswork out for him since he doesn't have any significant amount of experience in fitting.
So here are some questions:
1) I might ask him to try to do an extended seat tube like this:

With this kind of design, do you still need to have a seat post penetrate a couple of inches past the the top tube? Is this possible to do this with a lug? Would you trust an amateur to take on a job like this?
2) My fitter in the past told me that since I have short legs and a longer torso, I would benefit from a slightly sloping TT. I am 5'4" and don't usually have a plethora of space between the TT and my junk when standing flat footed. I've never had problems, but it'd be nice

Are lugsets that accommodate sloping TTs readily available? I'd want a very slight slope so it can still give a little bit more of a traditional look.
3) I've always wondered about this question, but was afraid that I'd get flamed for it. Oh well, it's time to ask. If an amateur builder and a pro builder puts together a frameset that only differs in things like clean brazing/welds, but tubeset/geometry is the same, would you notice any differences in ride quality?
Of course, I can ask my friend these questions, but I'd like to sound a bit more informed before I fire away. Any insight would be greatly appreciated!