Ben this always bothered me , I know you want to make 1 big continuinity , but it is easier to consider
the MOVIE , the Games and the Show 3 seperate timelines , or else it is a big headache and some times it doesnt make sense.
Well, think about it this way: it's completely true that when we first saw the Arrow in 1994 there was no thought that it might appear again years later or years. No one expected those stories would happen and it's entirely possible to consider the Arrow in Wing Commander III without any of that 'future history'. We certainly have the nuance to look at it there and work out what the designers were thinking and what they expected us to know.
At the same time and for the same reason, it's absolutely impossible to take the Arrow as it's presented three years later in Academy or twelve years later in Arena without considering its appearances in WC3 and 4. When you watch Red and Blue and you see the Arrow, you're seeing a choice to put it there that goes back to its creation, a choice to connect the reader back to WC3. It's a conscious choice to reference the thing that already exists and to connect to (part or all) of that lore and meaning. It's a progressive, iterative thing instead of a bunch of separate bubbles.
So taking that top down look is necessary, it's a lingua franca that's necessary for talking about stuff in a community. If you ask about the history of the Hellcat in general then the only way to answer that question is with the things we know about the Hellcat! But like I said, we've got the nuance too... we can go back and look at WC4 without Arena or WC3 and what things were supposed to mean at that point in the real world timeline. The Wing Commander movie using the idea of the Rapier for something new doesn't invalidate the story existing in the form it did at one point. And we can always drill down and think about that!
But there's a lot of contamination, too, because we tend to come up with a story we like and then stick to it without realizing. Consider the Rapier as you mentioned it! "Rapier II" is something that gets added in the Kilrathi Saga manual and it's the result of someone in creative services trying to combine the three manuals two years after the fact... Wing Commander I that has no designations, Wing Commander II that has American-style ones and Wing Commander III manual that lists those fascinating Roman numerals (Hellcat V, Thunderbolt VII) but not prefixes. They opted to strip the WC2 designations and in the process thought it would make sense to make the Rapier match how they thought the WC3 ships were being listed: the fifth model of the Hellcat, the seventh model of the Thunderbolt.
But that's not how either name was intended to work when it was created! Wing Commander II doesn't call it the Rapier II at all... the WC2 manual identifies it as the "F-44G Rapier" and it's only ever just Rapier in the script. The intent in 1991 was that it was supposed to be the seventh-plus iteration of the design; that it was brand new in 2654 but now it has a long history that we can assume. They didn't redesign the ship itself thinking it was the second one, they thought it was what it would look like after seven smaller cumulative updates over time (... with the additional request from legal that it move away from looking so much like the Firefox).
(It's worth pausing here because it's also super interesting how they tell this story. The designations in the manual themselves are all wonderful little stories told through your understanding of contemporary American military designations... the Rapier is the old one, the Sabre is brand new, the Broadsword is something new and special. But the Rapier story goes into the game itself: the similar cockpit, the lack of ITTS... you've got every department on the dev team working together to make sure people implictly know the Rapier is old! That's classic Chris Roberts tell-the-story-through-immersion!)
But then even Wing Commander III wasn't intending 'Hellcat V' to mean 'the fifth model of Hellcat fighter' in 1994. When the ships were dreamed up by Chris Douglas, someone with a complete understanding of how aircraft designations work, they had the American prefixes. They're visible in WC3 itself in the videos! F-90D Hellcat V on Rachel's console, F-103A Excalibur on the PAD at the bar, etc. So when the Hellcat was created in 1994 the idea was that it was the fourth model of a somewhat older ship that also happened to be the fifth ship design ever named Hellcat (like P-47 Thunderbolt/A-10 Thunderbolt II and the like).
So you see we can look really closely and say: here's the idea they had at this point... but it's often going to be very different from the one we've put together in our heads!
Hellcat is old but not that much , if you consider F44 Rapier was brand new in 2654 and in WC2 era the new ships Wraith and Morningstar are F97 - F95 respectively this means Hellcat is about 5 to 8 years old maximum.
What bothers me is for example F44 Rapier is brand new , it has a completely new look in WC2 and named Rapier II (even though for continunity we consider the original Rapier , Rapier II too ) but the designation is the same , so it doesnt make sense for Wing Commander Academy to have Hellcat with F-90 designation even if it is the V variant .
Also I dont see anywhere else the designation of the Hellcat V except for a brief moment in the png you uploaded, maybe it was a mistake ? I am not sure
Let's look at this in a few different ways!
You mention the Wraith and the Morningstar but their designations are both just from Star*Soldier, the same place as the F-27 for the Arrow. So if we just want to think about designations when the Hellcat was named, we can look at what existed then and why.
The prefixes were first established for WC2 in 1991 and like I mentioned earlier they're all intended to tell a little story about the decade between the games. The Rapier is old now, the Sabre is brand new... things like the Broadsword and the Ferret are new to Blair but they're older ship designs, the fifth iteration of each. So you're going in in media res with your character intentionally being behind the times.
F-44G Rapier
F-54C Epee
F-57A Sabre
P-64D Ferret
A-17D Broadsword
And then Special Operations added the YA-18A Crossbow in dialogue, which is a nice reminder that Chris Douglas knows his stuff!
At the same time they went back and retroactively gave designations to the WC1 ships in the licensing bible. They're all chosen to suggest that they're 'before' the WC2 ships:
F-32 Scimitar
F-36 Hornet
A-14 Raptor
Going into Wing Commander III they had knowledge of only those and they chose:
F-66 Thunderbolt VII
F/A-76 Longbow
F-90 Hellcat V
F-104A Excalibur
(I am certain Chris Douglas would've picked a designation for the Arrow but it has never surfaced.)
And we get a service date for each one!
Arrow - May 11, 2660
F-66 Thunderbolt VII - December 25, 2665
F-90 Hellcat V - September 12, 2669
F/A-76 Longbow - July 24, 2673
F-104A Excalibur - March 17, 2676
And what do you know, they match up to the designations perfectly! But it's pretty unsatisfying right off, isn't it? Because this is the version of WC3 that exists in Chris Roberts' head in 1994 which is set eleven years after Wing Commander II... it's only after the fact that the folks doing the manuals decide it's actually two years later but that's the version we know and that every successive story follows.
But just thinking about this tells us a lot about the intent which is still pretty fastinating! The Arrow has always been old, imagined to be fifteen in WC3! The Hellcat is an older ship but it's just half that. And the Longbow (3) is much newer than it's eventually presented as in Arena.
With that thought through we can unlock the rest of the continuity and look at these designations in the context of what comes later.
Which is also fun to do! I made a spreadsheet that might help which tracks the Confed fighters' known designations and the known bounds for when they're in service. It doesn't answer all our questions but it's a start:
https://docs.google.com/spreadsheets/d/1Y-ma6sYRA9X3N9E95xFubpcxzKabyn2hnWR0gy6JHVQ/edit?usp=sharing
And yes you can see all the wrinkles where one later creator misunderstood (or intentionally disregarded) a previous one. Scrunching WC3 into 2669 leads directly to the Star*Soldier designations. The Wraith and Morningstar and Phantom and such are in the 90s because they're all "new" shortly before the Excalibur which was a hard F-103. But if they'd been given designations in 1994 they would've been in the 60s, after WC2 but well before WC3. And we'd instead think of the Wraith being a contemporary of the Thunderbolt! Paths not taken.
But the same way you can go through and pick out the oddities you can come up with stories for them too... after all, real military designations are not exactly orderly, either. Maybe the Hellcat was the P-90 patrol fighter and was redesignated a fighter... maybe it was a militia design that wasn't adopted by the Confederation until later on... maybe there's an older numbering system and everything reset at some point like it did in the US in the 1950s... maybe it's something like the F-117 where the designation is there to confuse the enemy! Endless possibilities.