Debian is a slow bureaucratic political organization and works very hard to punish those who want too use it for business. Even if Cannonical had spent double the money, they'd probably get 1% of what they were able to do with Ubuntu.
>and offering support/consulting/employment to do so and it made Mark's intentions seem seriously dubious to me
Why should they not offer support to those who want too purchase it?
>although aside from the ad spying thing he hasn't really done anything egregious as I feared initially
The "spying" you are referring to is what Google Chrome and all the browsers do with what you type in your search bar. All Cannonical did was send your search queries to an HTTP endpoint. What are you searching in your app drawyer anyway that you don't want sent anywhere. It's not going to be anything other than the list of apps you have installed and all Linux repos can detect what apps you have downloaded from them.