Star Trek: Phase II

Star Trek: New Voyages (later renamed Star Trek: Phase II) is a fan-created webcast series created by James Cawley that is supposed to serve as a bridge between Star Trek the Original Series and Star Trek the Motion Picture.

James Cawley plays the role of Captain James Kirk in what's supposed to be the fourth year of the Enterprise's original five-year mission.

To date, seven episodes have been released - "Come What May" (the pilot episode) "In Harm's Way", "To Serve All My Days", "World Enough and Time", "Blood and Fire" (a two-part episode written by original series scribe David Gerrold), and "Enemy: Starfleet!".

Two short vignettes - "Center Seat" and "No Win Scenario" - have also been released.

Tropes:

All Just a Dream ...OrWasItADream: The episode "To Serve All My Days", in which Chekhov is afflicted with Rapid Aging to the point where he may have died, has a final scene at the end of the closing credits that may suggest that most of the whole episode was just a dream he had.
Book Ends: The beginning and ending parts of "World Enough And Time".
Bury Your Gays: Unfortunately, in "Blood and Fire". Kirk's redshirt nephew Peter is deeply in love with medical tech Alex Freeman, and the two plan to marry. (Everyone charmingly takes this for granted.) Alex ends up the last person alive on a doomed research ship, killing himself seconds before the Regulan bloodworms get to him. This was probably supposed to be reminiscent of Robert Tomlinson and Angela Martine in the TOS episode "Balance of Terror".
- It's also because the episode is based on a script David Gerrold wrote for Star Trek the Next Generation that kept getting punted into the wastebasket. For when the episode was originally envisioned, having gay characters in a relationship would be revolutionary, even if one of them died at the end. For the 21st century, well...
Downer Ending: "To Serve All My Days", which turns out to be just a dream.
Literary Allusion Title: "World Enough And Time"
Lower Deck Episode: The vignette "Center Seat" features Lt. Sulu and Lt. De Salle. (In the original series, De Salle appeared in three episodes - "Catspaw", "The Squire of Gothos" and "This Side of Paradise". )
Rapid Aging: Chekhov in "To Serve All My Days", with the older version played by the character's original actor Walter Koenig.
Special Guest: Walter Koenig as an older Chekhov in "To Serve All My Days", George Takei as an older Hikaru Sulu in "World Enough And Time", Grace Lee Whitney as Janice Rand, Denise Crosby as Dr. Jenna Yar.
The Stinger: The last scene at the end of the credits for the episode "To Serve All My Days".
Trapped in The Past: In "In Harm's Way", Kirk, Spock and McCoy learn that Commodore Decker survived his suicide run against the Doomsday Weapon, only to be sent back to the 1990s. He spent the last years of his life at the beginning of the 21st century, and left a farewell video tape for Kirk. William Windom, the actor who played Decker originally, reprised his role for this episode.
Year Outside Hour Inside: "World Enough And Time" has Sulu and a Red Shirt specialist transported to another dimension while the Enterprise was trying to beam them out of the Romulan ship inside a multidimensional spatial anomaly that they are trapped in. Sulu and the specialist apparently spent years inside that dimension during which he had fathered a daughter through her, which explains why he appears on the Enterprise as an older man (played by the character's original actor George Takei).