Hi Ryan,
Just in case, here goes.
Moodle is free and open source, using the GPL: https://en.wikipedia.org/wiki/GNU_General_Public_License (as open as you can get apart from public domain).
Yes, the Moodle community is large, helpful, well moderated and a great place to learn about Moodle.
Extensive plugins and themes database. It's also easy to submit and share your own plugins and themes as long as your code passes review both by machine first and then by an expert human. So plugins are of generally good quality.
Concerns
Re: "How does the company earn their money? Hate to see an unexpected bill down the road" -- Please see: https://moodle.com/ Moodle partners contribute financially and/or in code because it's in their interests to maintain and improve Moodle for their customers.
Re: "how easy do non tech people learn it?" -- It's a steep learning curve simply because most non-tech people are used to conceptually very simple websites; ecommerce and social media. Moodle has a long list of features, e.g. https://docs.moodle.org/31/en/Managing_a_Moodle_course and https://docs.moodle.org/31/en/Activities and so requires users to "think bigger" than the websites they're used to. I think it's best to learn how to use one or two features at a time. Here's an example progression of a typical use case scenario with Moodle: https://docs.moodle.org/31/en/Pedagogy#Progression I think Moodle's zero fee cloud option is great for getting people started: https://moodle.com/cloud/free/ (Full Moodle but number of users limited to 50, disk storage space limited to 200MB, and supported by adverts).
Re: "How is the freelance market? I'm trying to up my pay." -- As far as I can see, almost everyone who adopts Moodle and has a budget wants a customised theme. Moodle seems to be more difficult and more involved than CMS' like Wordpress and Drupal to write themes for so there's probably a fair amount of work out there if you can do it well, i.e. that ALL the features of Moodle will work as expected with your new themes. There's also demand for modifying existing plugins and developing new ones. I think it depends on where you are and who you know, as always.
Does this help?