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Thank you very much for this answer.  What I needed most is a good overall direction to take and you definitely provided that. I wonder if using canonicals to start 'centralizing' content might be a good way to round up the old versions of the site.  Yes, when I originally built the site it was by hand, each page individual .html and google still indexes those.  I removed them at the start of this journey and ended up with 24k 404s... who knew they were in that long!? Was great to hear of a similar experience... happy to hear more stories as well.

Thanks for the feedback!  As for hosting on separate servers, I have thought about going that route, but then I look at some of the larger networks with hundreds of sites if not thousands and I am not guessing that they are all on separate servers.  I could do the leg work of some reverse DNS to find that out (will update this post) I can see with spammy sites how the same server would hurt a network as it could quickly become a 'bad neighborhood', but I don't think google would likely penalize sites on the same network if the incoming links are from outside root domains and the site is of decent quality I feel like the answer to this lies in the inbound links and the content quality of the sites, but am looking for some hard evidence to support my thoughts. A good example is Smashing Networks series of sites... I need to do some research on that

You make a good point.  That depending on the project requirements and timeline, the extensions may not matter too much.  Great job on the quick rankings!