Reddit reviews 3,800 Early Advertising Cuts: Deberny Type Foundry
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Anytime I've done this kind work, I try and cheat as much as I can. Duplicating, offsetting and transforming can save a ton work. Also, as a general rule, building stuff in halves or even quarter and then mirroring will save me a ton of time. I'll usually go back with the crystallize tool and/or the warp tool to produce an 'illustrated' look and hide any mirroring or duplication.
One thing I would disagree with, that most people will tell you do, is draw it and trace/livetrace it. I feel the tools within illustrator are robust enough to achieve desired results without having to go through the process of sketching/scanning/tracing.
If you are looking for some great reference of this kind of stuff, this is a great book.
http://www.amazon.com/800-Early-Advertising-Cuts-Deberny/dp/0486266583
cheers!
edit: Adding link.