Good luck on your test Jacob. My shodan test was memorable and I value it greatly. But it was the experience that meant something, the belt just reminds me of it. It's kinda cool at first. Doesn't seem to matter as much after some years. Am still unable to leap tall buildings in a single bound.
Not sure about the uchi-deshi question. I think teachers would prefer a 'fresher' sort for uchi-deshi though. But if ya got the money, quit yer job and go train in Japan, ALLOT. That's what I'd do if I was rich anyway.