I think the game was never an easy place to be a new player and yet was still successful. I'm going to flat out guess that the difference today is that the pipeline of people giving the game a try just isn't working very well. It might be worse to be a new player now because numbers are lower and the game lacks the energy it had when hundreds were on in 2 main arenas but it was always a challenge and I would guess that a lot of people who tried it out got bored real quick with dying after long, (more than a minute,) flights to their death so the retention of a player who made contact through a free 2 weeks was maybe low compared to other games even back then.
I think there are several things the game could have that would help with retention, I think of lot of potentially good ideas have been suggested, (I've long thought that an easy way to practice shooting at maneuvering drones would help get people up to speed,) but I am not sure that if the conversion rate went up it would make as much of a difference as an increase in simple raw numbers of two week trials would.
I'm not a video game player so its only intuition and youtube videos that inform my thinking. From what I have read War Thunder's FRB is a ghost town most of the time, and you need track IR unless you are unusually skilled, The ATAG server, (IL2,) boasts of 100 player capacity. I don't know ROF's numbers but the couple times I tried they were low, DCS I don't know anything about because it tried to break my computer, (if you have the hardware it is supposed to be hip.) If AH is going to remain AH I would say that those are the competitors and the active player base across those games seems like it is really small, they are all niche games. I am not considering War Thunder aside from FRB to be a competitor to AH in the same sense that I don't consider shooter games or Arma or any of the other titles I don't really know much about to be competitors.
Except for players with, by my standards, freakish skill, I consider AH to be a joystick game that is more about simulating the physical, (manipulation of stick and rudder plus throttle,) than it is about controlling a game airplane with a computer. Does that make sense? I think that this is rare. Even within AH the way tanks and level bombing is controlled strays from this, I would argue in part because there are not any generally available physical controls that model the real life controls for those aspects of the game. The reason why I like the absence of carb heat and radiator flaps and other IL2/DCS (from what I hear) "realism" is that those button pushing features have no tactile reality and in fact interfere with my suspension of disbelief. In my view this introduces a real quandary, the best thing about the game is also the greatest barrier to experiencing it well and subscribing after a 2 week trial.
I'm just going to go out on a limb and assume that joystick sales are on par with VHS recorders meaning that the background hardware environment that supported a higher number of try outs and conversions for AH has gotten really bad. I seem to remember that AH had some kind of deal with a joystick manufacturer to give free joysticks with a subscription but since its long gone I'm assuming it didn't work. The problem as I see it is that at the moment AH can compete against the other combat flight sims that aren't arcade but the whole genre has trouble generating leads when competing against games that don't require any special hardware.
What I don't really understand is that, even given this hardware obstacle, why the raw growth of the number of people with computers and internet access hasn't expanded the number of potential players enough to soak up the change in tastes. When I look at Civil War Reenactors I feel like there must be at least that many people World Wide who would play AH. To me this suggests that there are still plenty of potential new customers but they are clearly harder to reach.