Rhyoth...interesting thoughts...some I had never considered and will try to incorporate in the future.
As before this will be the first main season we have run it with chances of more than one or two leaving for the entire league. Previously it has made little impact but I see this season has potential for on or two teams to lose, or at least buy back, one or two players each.
I will go through your points and either explain decisions of totally steal your ideas
1) Skilling up a player can be long and painful, and it's always frustrating to see your veterans leaving your team.
This was a major concern while designing the table. I wanted people to feel like each player could leave but also that even skilled players had a chance to stay. A little bit of league history. Originally started with 3-4 players just playing in an Open season style, organise and play who you want, when you want. This helped grow the player base and once we had 10 meant we could run the structured system. So at the moment (and the foreseable future) we will always run 2 leagues. One organised and one more casual. The casual we do not run the leaving rules. So that was how I got around the threat of leaving players. If you dont like the chance, play in the casual (Open).
Concession here though. IF we have a large player base (say 20+) it would probably make a difference. Being a small town with a limited player base it has added...SO FAR!!!!...lets wait until the start of the new season..big test there
2) There will always be one unlucky coach who will roll only 6 when he shouldn't, which will make him start a new season with nothing but 6-7 lineman and a whole team to buy (again)
Again something else I considered. This was the biggest sticking point for me as I saw myself being that damn coach

. Anyway after much thinking and post rule referencing (went through old BB magazines all the way back to Star Player addon for BB Version 2

) I found something similair to what you are talking about with a compensation for lost players OR replacing with free positional (ie lose a 50spp Blitzer, gain a new Blitzer for free). But than it occurred that when those rules where in place there was a limited Inducement and Journeyman system.
With the current inducement and journeymans I dont think it will be TOO much of a problem. I am in a position where I will probably lose my 2 runners in the Norse team and MAYBE an Ulfwerener....so in my league I will be the first to see how it effects people. This is still a concern for me and can understand your thoughts there.
3) I think your second table need a complete revision since
2 parts to this one. Dont agree on the first part about the only reason to not retain is if you cant afford them. By making the coaches roll on the highest SPP player first and RESOLVING that player completely before moving on it means that the teams with multiple players have to decide to keep that one star, or 2-3 lower. Its a risk. Admitedly the teams with more cash can keep more players but most teams will only need to roll on the table after their second complete season (8 games per season) so most teams effected will be the higher value teams. The lower teams only have to roll on one or two and most of them are only just in the area where 2 sixes will remove them.
The second part about the ageing table. Pretty cool concept. I wanted to incorporate that at the start but than figured, ah we will see how it goes. I LOVED the ageing tables and was disappointed to see them leave. That isnt bad at all, and than rolls over with the added rolls for the next season. Interesting. I like the concept. I will wait and see for after this season to see if I can incorporate it. I even like the idea about incorporating that in as an extra column....hmm..got me thinking there.
Your final part 4 comment needs more thought than I can handle right now. The idea about the faster developing teams retiring more players is correct. The part about the slower teams having the fear of mass retirement is also warranted. But than here comes the main reason I wanted to do this. I LOVE team management and wanted more of it. By KNOWING that you have to make the rules you can start saving cash, firing and replacing earlier to give players a "cycle", any number of alternatives.
So in short...LOL..most of your comments are still fresh in my mind and I am waiting till after this season to see how they work. I do like the ageing one though and there where some "concerns" that I hadnt seen yet...so thanks and that post was perfect to get my brain working and look at things in a way I hadnt.