I can't comment on either brand of cabinet, but I picked my KD based on personality. I wanted someone who would listen to my ideas and not just say "yes" but, rather think about if they made sense and what the options were. Of course, she told one of the contractors that I had too much time on my hands because I got too many ideas from the "internet". Hahahaha - that's a huge GW shout out!!!!

I might be concerned about the "old school" aspect. It's hard to know without hearing more details. Does "old school" mean she won't do frameless cabinetry? Does it mean she is still doing pull-outs instead of drawers? Or not knowing about the latest in appliances? Does she understand there are more choices in sinks than stainless double-bowls? What about countertop templating? Does she only do 4" backsplashes? Is she knowledgable about undercabinet lighting? These are a few things that come to mind when I hear "old school", which could be issues for you.

Mgoblue, LOL on the "internet ideas". It is important to have a good working relationship. Ak Chicago, you bring up a lot of points that I had not considered yet. My first thought is that the only old school about him is the fact he hand draws rather than computer modeling his plans. But definitely some food for thought. One question that an answer alludes me is whether there is any difference in quality between Belmont 1900 and Custom Cupboard. Thanks for weighing in!

Can't advise on brands- ask each of them to explain. Even if tthey don't know the other brand they cantell you what the sales points are on the one they have. Let them talk, use it to find out about them
Picking a KD-will they do your kitchen
How do they deal with initial plan? One, multiples, or rough draft and discussion? Do they tell you when you can expect to ssee changes or do you wait for a phone call? What do they do for follow up? Do they want to see your current kitchen? What kinds of questions do they ask? Do they explain things clearly? Do they order a sample of your door/color? What do they think is important? What is follow up? See what fits.
Pencil means little unless you really need 3D. If you are looking for really accurate renderings find out if they can and will do that. Few do and it is very time consuming. Actually pencil likely means they can be good with the details of fit and have some mileage.

All the rest matters little. Your on GW, can get all that here so you can go in and torture em :)

Hand drafting is good. They are thinking things through. Often times, when using the automated software, things get missed. Things look so done and beautiful before they actually are, and it interferes with the thinking process. I wouldn't hold that against him at all. It could be a good sign, imo.

You could always DIY or find someone to 3D the final plan for you. There is software out there that homeowners use, so it can't be that difficult, unless you are not computer literate to begin with.

Good points on making sure they are up to date with other things though!