In general i understand most of the times we use kun readings for standalone kanji and On for compounds. I just came across 春休 and apparently its pronounced with the Kun-Kun reading. So why not Kun-On since 休 has the On reading and its grouped eg 春休み？Also for example今年. Why is this ことし using the On-Kun reading? Is there anyway i can differentiate when i use which and which to pair each kanji with? Because of this the general rule i learnt of using onyomi for grouped kanji doesn’t seem to align so much anymore and its giving me issues reading sentences. Does anybody have advice?
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There are only general rules, like the ones you learned, and they are generally very useful, but as you have experienced, there are many exceptions to those rules that don’t have any rhyme or reason behind why they’re read that way, or that reason was lost to time.
In those cases, the best way to proceed is to learn the word as a word, and not a combination of kanji.
When you know the word, you have learned the reading for that word, so you don’t have to guess which kanji reading to use.
Words that are originally from China usually get the onyomi (also called compound words, so words with two kanji together), and words that have hiragana characters included in them (like the ‘mi’ in 休み) usually get the kunyomi. But obviously this isn’t a hard and fast rule. You’ll start getting the hang of it the more and more Japanese you learn, so the best thing you can do is learn a couple vocab words for every kanji, at least one of each reading, and go from there
You just have to remember these as you encounter them.
You already got the basic answer (i.e. these “rules” aren’t really rules, just tendencies), but I do want to mention that 今年 isn’t on-kun–it’s kun-kun, with こ for 今 being not from the on’yomi of コン, but rather [from the same root as これ/この](https://gogen-yurai.jp/kotoshi/#:~:text=%E4%BB%8A%E5%B9%B4%E3%81%AE%E8%AA%9E%E6%BA%90%E3%83%BB%E7%94%B1%E6%9D%A5,%EF%BC%89%E3%80%8D%E3%81%AE%E6%84%8F%E5%91%B3%E3%81%A7%E3%81%82%E3%82%8B%E3%80%82).
You don’t. You never use a reading, ever. It’s not how the language is read.
Words have pronunciations but kanji do not. The readings are just the complete set of pronunciations they have when being used in words, much like writing out all the myriad ways that “e” is pronounced across all English words.
Learn words. Words have meaning, use, kanji spelling, and pronunciation.
Youve already gotten plenty of good answers, but just to reiterate:
Forget about rules (other than the one you mentioned with solo kanji vs compounds, which does give you some idea but still isnt 100% certain) and just learn individual words.
Given some kanji have several readings, reading a compound sometimes feels like a guessing game and dwelling on that is a waste of time. Not even natives know how to correctly read a new word theyve never seen before, they can try to guess but odds are theyll just look it up and move on.
You’ll just know. With enough vocab, you’ll just know which one to use but generally you’ll use the ony reading with hiragana and kyu reading with kanji + kanji