The two expressions have similar usages, but -도록 is often used in figurative speech too while -ㄹ 정도로 is not. -도록 has two uses, describing a desired state (다음부터는 주의하도록 하겠습니다) and making a figurative comparison (목이 쉬도록 소리를 질렀다 = doesn't mean the speaker actually lost his voice). The second usage is usually a set expression and the listener doesn't take it seriously. -ㄹ 정도로 is mostly used in the first, more serious sense of -도록. For example, here are exaggerated expression of -도록. -ㄹ 정도로 is rarely used for these, because they are not meant in the literal sense. - 입이 닳도록 잔소리를 했다. (until one's mouth wears out) - 프로젝트 끝내느라고 죽도록 일했다. (worked oneself to death) For cases of describing a desired result, both are fine. - 컵이 반쯤 [차도록 / 찰 정도로] 물을 부으세요. As for your examples, the first two are how we say it all the time. The third one is border-line unnatural, and the fourth one seems slightly better than the third.