Honestly I think there's a general problem.
Many people simply don't invest time for AirwaySim - that means choosing airport and aircraft as well as routes properly. And they don't read the forum, the FAQs and so on. They simply don't learn from their fails.
"Lack of skill" is a bad term used in every multiplayer game. It has a very bad reputation but at the end of the day it's the hard truth.
I really like your ideas but they are only minor changes. It reminds me when Blizzard changed the difficult system of World of Warcraft. It went much easier and still the Casuals (a not so bad name for the Unskilled and Newbies) weren't able to kill every boss.
Lots of people simply expect to join a game and be good or at least above average. Some may try several times, mostly if it's such a good game without real alternatives like AirwaySim. But if they fail again and again they leave.
However, there are also some players who join the game, invest time, and run successful airlines from start. But it's not possible to get everybody on this skill level, mostly because that means people have to take care of their skill by themselves - at the end the same problem why there are not 6.8 Billion soccer superstars or University graduates around.
There was once the idea (mostly before I wrote my FAQ) for a mentoring system. Good players take care of a bunch of Newbies, sharing some strategies but mostly help during the gameworlds. The idea wasn't followed because most people ask for help but won't be helped.
I receive lots of PM from people who want help and I always answer as good as I can. Only a small amount of people follow these advices and really benefit from it, the others are still at the bottom and fail again and again (I remember the famous bogglie14 threads as a good example: http://www.airwaysim.com/forum/index.php/topic,31531.0.html
That leads to another problem. It's not only about the newbies. Take a look at Jet Age. 95% or more people using CV-240 as their (only) starting aircraft are unskilled, run (below) average airlines etc. A lot of 'old' and 'well known' players are part of these 95%.
I can understand some people (quote from a PM) "Just want to play from day to day this time" but it's still a stupid choice in nearly every case.
Maybe the post is a bit confused, I'm really sick (literally :/) and had to pause several times, but one thing at last;
The problem with lots of unskilled people, (below) average airlines and newbies without any interest affects even the really good guys. I know lots of extremely skilled people who simply lost interest because there's no enemy, no fighting.
I was very happy when I saw Iksu sharing base with me in Atlanta but I got disappointed. Same for ORD in Jet Age now. In DotM I stopped playing my airline 4.5 years into the gameworld, it's on autopilot till then and with 70 billion value 2x bigger than the second biggest airline. That's a joke.
There's no fun in Newbie-Bashing. It wasn't fun in Quake, it wasn't fun in Counter-Strike, it wasn't fun in World of Warcraft and lots of other games and it isn't fun in AirwaySim.