After reviewing a few more articles on this topic and the Bitcoin Whitepaper conversation on the cryptography mailing list some more interesting details have emerged. Satoshi's last email on the cryptography mailing list, where he publicly says to James Donald, "I sent you the main files". These files were the Bitcoin source code for the first Bitcoin client software. Also, we can see from the Hal Finney private email that the subject heading reads "Re: Bitcoin source files attached" with James, Hal and Ray Dillinger cc'd.

Therefore, The private Hal email confirms Satoshi likely sent the Bitcoin source code files to not just Ray Dillinger, but James A Donald and Hal Finney too on November 16th, 2008. Satoshi had apparently been working on this code for more then a year and a half. This likely means Satoshi began working on Bitcoin code in earnest around the middle of 2007.

Also, according to the above Bitcoin Insider article "The source (v0.0) also has a discarded genesis block in the code which has a completely different hash. Assuming the hash was the first genesis test block, it was produced on Sept. 10, 2008." This may be an effective timestamp for the date of this v0.0 source code. This implies Satoshi gave these three gentleman an older "version 1" copy of Bitcoin, and not an updated version 2, which could have been v0.1. (In one email Satoshi describes a new Bitcoin feature as a "version 2" issue).

Speculation on why Satoshi didn't give these three people the full version 2 details: Well, James A. Donald made it clear in one of his cryptography mailing list emails that he wanted to launch his own Bitcoin version eventually. So maybe Satoshi didn't feel like sharing everything with someone who may front run him to the finish line?