The Data Merge function in inDesign is great, learn it and embrace it... anything to never need to use word to do a mail merge ever in your life.
Here's a tutorial from Adobe that sums most of it up:
Adobe - tutorial : Use Data Merge to build personalized documents
MD
Visit exhibitions. Read magazines, read books and above all enjoy it.
Call a few designers, see if any of them would like to be a mentor (most have egos that would love this :)
good luck.
Letterpress or Litho?
If you can go the Letterpress route, that would make a nice change.
As for the orange, it's difficult to see what orange you're thinking about without seeing the colours in the flesh. The right choice of grey and orange could work very well.
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