"I am tempted to say that a doctorate in AI would be negatively useful, but I am not one to hold someone's reckless youth against them - just because you acquired a doctorate in AI doesn't mean you should be permanently disqualified." Eliezer Yudkowsky, So You Want To Be A Seed AI Programmer

How should I interpret the above quote? If someone has to be able to follow the advanced arguments on Less Wrong to understand that an advanced education is disadvantageous yet necessary to understand this in the first place, how does Less Wrong help in deciding what to do?

Your line of questioning here just seems strange in the context of the quote. The quote seems straightforward and not even all that relevant to whether lesswrong is useful for people who struggle to understand lesswrong. To the kind of people who have even a remote possibility of doing useful work on a seed AI it is just a trivial statement of Eliezer's personal opinion. While many don't agree with him Eliezer has written elsewhere on his opinion on academic orthodoxy as well as his own development with respect to approach to AI. Such opinions can just be taken with a grain of salt as they would be from anyone else.

This is just an example of what I experience regarding Less Wrong. I'm unable to follow much of Less Wrong yet I'm told that it can help me decide what to do.

There is value in making things as accessible as possible where this can be done without sacrificing the depth of the content. At the same time there are always going to be people who are not capable of following content of complex topics, whether that be on rationality or anything else. Ultimately all communities whether online or off have a target demographic and are not for everyone.