That would be me, sir. And practically all of these have been addressed before.
Difficulty: I designed it to be fun for myself, I'm sorry for your poor flying skills. To rectify this, I am currently designing an easier plane track themed after early 20th century air races.
Getting back into the air: This is a problem with the checkpoints currently, they were not designed for planes (soon to be fixed).
Hard to tell which direction you're going: I kind of forgot about this one while building it, as it's hard to get lost in your own map. Will be rectified soon. Maybe.
Missing checkpoints: Do you mean the lack of checkpoints on the lowest parts of the map? Fly, don't drive.
The music: I think it's good, sorry. Nor am I to blame for it.
You know, with all the people having difficulty flying, maybe I should write up a brief tutorial on how to fly properly.
In all fairness, the vast majority of players aren't video game flying prodigies like you. If you hit a tree in your map, the punishment is real. That's just too harsh for a racing game, man. It's coupled directly with the checkpoint problem with flying.
And to the missing checkpoint thing, i was talking about physically missing checkpoints. I don't think I delved into it enough though.
On an unrelated note, if you join a game late/die, you should be able to (re)spawn and play anyway, unless there's a conflict with car spawning.