I think that comparative to WordPress you are very correct, DotNetNuke is much more intuitive (I don't know if that has anything to do with the fact that I have used DNN much more than WP). To add a bit to your statement about the DNN Community, you will find that you really have to focus your questions here in the DotNetNuke community forums rather than any others. This is the best place for advice on anything DotNetNuke related and the response to questions here generally happens rather quickly.
You may be a little correct in saying that there are more technical people who use DNN rather than WP, but that is by nature of what you can accomplish with DotNetNuke. You aren't going to try and build an eCommerce site that need to be load balanced with WP, that is not it's core competency. DNN is a much more powerful tool for building very robust sites with little to no change out of the box, which sometimes does require the help of more technically savvy people.
The modules that are available for DNN can for the most part be found in the DNN store, and with a few clicks you can read reviews which will give you some insight on the module and developers. The storefront site does a great job now of displaying top developers and modules.
While DNN creative may be more expensive than what most people want to pay for video tutorials, it can be a very valuable resource and prove to be more that worth the subscription cost.
All in all, I think you have made some very valid points, but I would recommend focusing your questions here in these forums. You will find the community members here to be very passionate about DotNetNuke and inviting when it comes to new members of the community. I have never been steered in a wrong path coming here.