Hi, I'm new here but not new to big business.  Here's my take on this promising enterprise:

1. The benefit:  You are getting rare and valuable trees at a very low cost.  Much lower than normally attainable.
2. The setup:  James has plausibly explained how he can achieve these below average costs and how it is a win/win for everyone. 
3. Initial credibility:  James has already established himself as a reliable source with his cutting sales.
4. Initial investor pay off:  I believe that everyone had received their $2 cuttings in excellent condition and I haven't heard of any complaints or mislabeled varieties.  Perhaps delivering a couple of trees would truly help with this element.
5. Communicated Successes:  I could see where a little more could be done here but he has been supplying monthly updates for the last few months so I applaud the improved communication.

Overall, I think this plan has a wonderful chance to succeed.  As long as orders keep trickling in to keep the heat and lights on, there shouldn't be any problems.

Best Wishes,
Chuck