i think you're absolutely correct, but as you said, you need to know what you're looking for...... but more importantly, with vintage tools, you need to know exactly what you're looking AT. that's why i gave him two that are quality and pretty much come ready to use right out of the box.
with your experience, i'm sure you can tell crap from treasure with one quick glance. a little more difficult for a guy new to hand tools. know what i mean?
Actually I don't, and here's why: I love my L-N stuff, but for what they cost I can afford to make a few purchasing errors several times over. I think that for someone just getting into hand tools, buying L-N off the bat is akin to installing lockers and a 4” lift when you’re just wanting to try wheeling to see if you like it. Also for the price difference, even if there’s no life left in a plane’s iron, you can get a replacement blade (or other stuff) cheap enough. I collect tools, so yea, I do evaluate stuff at a glance to see if I’m interested from a collecting standpoint, but there are a lot of usable tools to be had out there that don’t require anywhere near that level of knowledge and there are a lot of FAQs out there to help out.
By looking at completed e-bay auctions, you can get a sense of current values. For user qualit tools, watch out for cracked or repaired casting, loose parts, rough or missing totes and knobs, and iron’s with little life left (less than 1”) Don't worry about percent of original finish, repainted is fine as long as there's no red rust You can educate yourself as to basics in an evening with the search engine of your choice.
So lacking more specific info as to intended use, for general bench work I’d recommend the following:
Bailey # 3 or # 4 Smoother Plane ($30 - $50)
Bailey # 5 or # 5 ½ Jack Plane ($40 - $75)
Bailey # 7 Jointer ($80 - $120)
# 9 ½ Block Plane (The only tool I’d buy new from Stanley)
If any of these have a C after the number, that is fine, it means the sole has been grooved to reduce friction. All the Baileys are from Stanley, it’s an omage to the inventor of the mechanism. For simplicity, stick to these models (there are variants but that’s going to muddy the waters) and to planes with wooden totes. (By the time they went to plastic, the quality went downhill)
I can’t help with spokeshaves without knowing the intended use.