Applying potentially the best planning & executive advice I ever received (thanks Carolus!!), I sought to identify the last step and work backwards.
Importing Evernote Data into WordPress
The last step in the content uploading process is transferring Evernote notes into WordPress. Though I didn’t want to get ahead of myself, I wanted to know something about how this works up front (or else I would have to abandon using Evernote for the beginning!).
There is a plugin (Import HTML Pages) that takes html pages with tags and converts them to WordPress. Reading forum websites suggested this plugin as a solution for importing Evernote posts. It seems to work as such: an Evernote Note is exported as an HTML directory with attachments; the plugin specifies which HTML tag (most like <div>) that has content and the HTML tag (most likely <title>) that contains the title; it also uploads the images and other attachments included in the HTML file; it claims to even fix internal links such as a “Next Section” link that connects Notes in a linear fashion; and it allows both categories and tags to be applied to all of the future WordPress Posts or applied selectively through a custom HTML tag.
Importing Word Document Content into Evernote
My second technical challenge was finding the most efficient way to upload text from Word documents into WordPress and not directly copy what would likely be over 200 posts. This took a couple minor experiments, but I learned that Word Documents are only included in Evernote as Attachments and dropping a .txt file into the Evernote application item in the Dock would convert the file to a new note. Thus, by converting my six thesis chapters into .txt files. I could create six corresponding notes in seconds. I could then rely on Evernote to divide each chapter into smaller posts and to attach tags for sub-topics addressed. Once I realized that not only .txt files work like this, but rich text files (.rtf) that maintain the formatting and tables, this task became much less daunting.