My response was mostly to your last sentence, "The more times they have to click 'yes' without thinking, the more susceptible to malware they become." There exists a dichotomy of you click on a link, it loads the page or begins the download or alternatively, you click the link, Little Snitch checks its filters and if it doesn't have a rule set, it'll prompt you to set one. In no case is the second one going to make someone more susceptible to malware, because the worst case scenario, where someone approves every single download, results in exactly identical outcomes as the person who does not have Little Snitch installed.

I agree broadly with your point that prompt fatigue or decision fatigue is problematic and should be avoided when possible. I think this is a problem in particular with Little Snitch even, which doesn't do enough to provide. However, the point of Little Snitch is to allow someone to monitor and control the traffic at a granular level and the consequence of providing that utility is the frequent prompts whenever you're visiting a new site. To Obdev's credit, silent mode exists and you can set it to deny or allow all traffic without a prompt (and evaluate the traffic at your leisure).