Dennis Bailey mentioned me... and since Tin Man is among my favorite Trek episodes of all time, the least I can do is respond. (Tin Man got a now ex-boyfriend of mine to try TNG at a time we were dating and he was a TOS purist... )
As far as I'm concerned the details of the presentation are irrelevant. FUND PHASE II! I WANT MORE! The heck with who did what when! I don't care!
But, responding to Dennis's question... Arguably, the oldest Star Trek fan film still in active production is either Yorktown (but not in CONTINUOUS active production) or... if you consider Star Trek Continues a continuation of Vic's Vintage Voyages... it has a claim. Vic started playing Kirk when he was about 9 years old. Also, Hidden Frontier still releases an Audio episode once in a while, and it's the continuation of VoA... so if you count VoA and their audio... you can argue. Finally, Exeter started before Phase II and completed their second release after Kitumba, so you can claim that, too, if you want to get sticky. If you consider all of George Kayaian's productions as one, Multiverse Crisis/ST: Antyllus has a claim, too.
But if you only look at high quality continuous FILM productions, from ONE production company, of One series and only at multiple episodes with vaguely regular releases... they'd be the oldest still producing... that I know about. (The reason Star Trek Reviewed is the largest collection is I never take the position there is nothing out there I don't know about. I was just lead to a high quality TNG-era Trek fan film series with 9 full episodes, each over 30 minutes and less than 90 minutes long. Sadly, you have to speak or understand Czech to enjoy it. No English or other subtitles. I have been told by Czech Trek fans it's even better than Metrinsky Incident. I'm going to try to get the producers of "Star Trek: Bohemia" to add English subtitles! I'm a viewer, not a filmmaker!) If you count Phase II from the time James started building his sets, that extends their time period from 1998 to 2014, a period of 16 years. That would make the Phase II film production far longer than Hidden Frontier FILM production. It might also be OLDER. (But not older than George Kayaian, who was not doing the TOS crew). Phase II shows no sign of stopping either. So I think it WILL BE the longest in FILM production by any reasonable measure pretty soon... (again, there's George, who is also still producing. George is the top of what I call 'garage production.' But it's not what I call 'professional production.') Even without the set build, 2003-2014 is 11 years, which is comparable to the period HF produced films.
The oldest fan film without regard to quality featuring Captain Kirk and Mr. Spock that I know about is "Star Trek: The 8 MM movie." It was produced in the summer of 1967 by children using daddy's camera, no sound, ... (the music was added much later). It depends on what you want to count.
http://www.break.com/video/ugc/star-trek-the-8mm-movie-1848482 2 minutes, 59 seconds.
If anyone knows of a Star Trek Fan Film produced over Christmas in 1966... well, there COULD be an older one!
As far as I know, Star Trek Phase II is the oldest Star Trek Fan Film featuring Captain Kirk, Mr. Spock, Bones McCoy, etc. which MOST PEOPLE consider high quality. I realize DoubleohFive doesn't consider them high quality. Doubleohfive has his opinions, there are also 'truthers' claiming Sandy Hook didn't happen. Everyone has opinions. Some people put their real names on their opinions.