Time to add some inexpensive HP

Please excuse the stupid questions: I am learning this as I do it.
For an electric choke, do I have to run the wires through the firewall or can I get 12v under the hood?

A 12v keyed source under the hood is what you want.

Are used cams out of the question? (there's a guy selling a used 340 cam for cheap...).

As long as it is in good condition, nothing wrong with used. You will need new lifters and follow the breakin procedure. New valve springs would be a good idea as well.

Looks like new timing chain is do-able.

If you get a new chain, make sure it's a double roller, much better quality than the factory original.