We are working right now on JargonBot, an LLM tool that suggests glossary terms for a given post. We're ironing out the details of making it a smooth process for authors to sanity check it and giving final approval.
I do kinda expect it to be a game changer for how people can relate to the site.
I'm a newish user, but I think it was good for me to keep hyperlink-chasing early on. It helped keep my early use of this site primarily learning-oriented rather than interaction-oriented.
There is, in the left panel under "Concepts" link. https://www.lesswrong.com/tags/all.
I'd guess you haven't seen "Rationality: A-Z" (also called "The Sequences") from that site panel as well. It builds up many of local concepts from certain starting points over course of many essays, gradually increasing level of material. For a newcomer, it is rather common to be linked to some essay there upon some marker statements (for instance, "that hypothesis is improbable, but its alternatives are no better so I keep 'my' one!")
https://www.lesswrong.com/tag/r-a-z-glossary
I found this by mistake and luckily I remembered glancing over your question
it would help newcomers