This will be my first time using Illustrator, but I thought I'd jump right in and have a go at recreating this old poster:

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Update 1 - 13/5:

So, this is pretty fun! So far I've been playing around with building free form and with shapes to get the main areas of the poster mapped out:

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Update 2 - 21/5:

Just the city left to go now.. I've mainly been playing around with the pencil tool for this next bit of progress, and a few different brush strokes for the trees in the background. For the big tree in the foreground I've been using the minus-front tool to cut out some leaf definition.

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Update 3, 3/6:

I followed the make-your-own repeating pattern video to create the city background. It's not perfect, but I think the effect is about right. Also fiddled around with some of the text to make it a bit closer to the original. Phew... just the centre to finish off now.

(Oh, and where the patterned section collided with things in ways I couldn't get around, I used the blob-brush to do some cover up I'm not so proud of..)