Google Books recently scanned most of Gregg Writer Volume 2 from the Harvard library collection. The scan includes October 1899. It also includes February through September 1900. November, December, and January are missing from the Harvard collection and were not scanned. (For Volume 2, the magazine ran from October 1899 through September 1900.)

Google Books Originally posted this scan as snippet-view only. I emailed the Library Project and asked why a magazine from 1899 through 1900 could not be downloaded. It is obviously in the public domain. After a month, they emailed me and told me that they opened it up for full download. I have included the link at the bottom of this post.

I have also included the link for Gregg Writer Volume 2, October and November 1899, from The Louis A. Leslie collection. (This scan also includes issues from Volume 3.)

If you put relevant pages from both of these scans together, you will have the full volume, except for December 1899 and January 1900.  For the October 1899 issue, I recommend the pages from the Leslie collection, which are scanned in color.

These issues include very crude shorthand plates, which mostly consist of business letters.

There are a few interesting items in English:
—Page 16. An article about a stenographer who was poisoned to death by a typewriter ink ribbon.
—Page 70. An article about the fire that destroyed the Gregg school offices in Chicago in January 1900.

Here are the Gregg Writer Vol 2 links:

Google Books link to Gregg Writer Vol 2, October 1899 & February-September 1900:

https://books.google.com/books?id=guNDXraeNgQC

Louis A . Leslie Collection Link to Gregg Writer Vol 2, October & November 1899:

https://cdm15457.contentdm.oclc.org/digital/collection/p15457coll1/id/329/rec/5