How is it that some of these are out of chronological order? Episode 27 came out in 1985, between Episodes 9 and 10? Episode 39 Came out in 1986 between Episode 13 and 14? Etc.

That's because this torrent orders the OVAs according to the episode ordering used on the story section of the official Cream Lemon homepage. Strictly speaking, the original Cream Lemon is only comprised of eps. 1 to 16, After that comes Shin Cream Lemon, produced by a new staff, which is equivalent to ep. 17 to ep. 25 here, with 9 OVAs in total. After that, the other releases are not, strictly speaking, Cream Lemon directly but adjacent products. For example, ep. 38 is from 1987-06-25, but it wasn't originally released as part of the Cream Lemon series, but as an special. Something similar with Ami Image - White Shadow, Ami Sorekara, the Mangaka Series, the omnibuses and the 1992 and 1993 OVAs. To be precise, under that logic, Tabidachi - Ami Shohu should be here as well, but it's not included in Cream Lemon's homepage, hence why it's not here.

I made a mistake regarding my comment about Tabidachi. IT IS INCLUDED in the official website as tale/episode 39. As to the reason why it was added at the end as ep. 39 in the website despite being released in 1986, it's probably to emphasize that it is the final story of the Ami saga, so it was put there for that purpose instead of putting it in the correct chronological order and confuse the public with Sorekare, which wasn't produced by the original staff, did not have the original seiyuu, was not well received in Japan and has not been iterated or mentioned in further Ami-related products like the 1994 PC-9801 game (which has the original seiyuu).