Biggest problem would be, as an example, the Spit drivers.
You need to fly the Spit I for so many hours then the Spit V, Seafire IIc, IX, VIII, XVI, XIV.
Same would apply to the 109 guys.
All the uber rides whacking the 109E drivers might be a bit discouraging for a new guy
You'd probably be better off with 3 arenas, Early war, mid-war, late-war, but I know that's also not an option so we're going to have to live with the fact that 90% of the AH drivers will be in LA7, Spit 16, N1K, P51, Tiffies or the big cannon Hurri IIc
If you can get yourself to the point where your score doesn't matter, and you don't take losing a fight personally, then tooling around in a less then uber plane can be fun.
As one who dies often in my old 38G I can attest to the fact it can still be fun, but every now and then you want to just shake your head in disbelief at all the LAs and 16s