Some great points, Wagner.
As for the whole schedule being done before the season starts? I probably wasn't clear but yes, absolutely. I visualise the schedule being listed later this season with something denoting the team within each matchup whose responsibility it is to 'challenge' the other team via the PickUP (PU) method.
I see that you have asked demars about whether it is easy enough to organise or randomise the matchups. Great.
I'm thinking that we could do the following:
1. Lock in 14 teams.
2. Have 1 division based on Team salaries for the first season. I know it's not perfect but it's probably accurate enough to begin with. We can change for 2nd season.
3. Start confirming those 14 teams - make sure they are still on board - have 100% HG rosters - will be ready to play at the start of Season 68 - get total team salaries (can be adjusted this season as necessary)
4. (CRUCIAL) We ask them to predict what their Team Salary total (Buzzer Manager is helpful here) will be by the start of Season 68. This will be difficult, there will by inconsistencies, but if we don't start somewhere, nothing will get done.
5. Using all of those predicted salaries we at least know what the league is going to look like whether we have rankings or not. (BTW, when I referred to rankings before, I meant the end rankings after LEague 1 was completed - which could be used to setup League 2)
We are going to have a lot of little problems along the way. However, until we lock in the number of teams for the first League, we can't really move forward.\
I suggest we start with 14 teams and that we conduct the first season's League ("The League"

similar to how BB does its leagues. I think managers will find this easier and friendly to begin with.
So, 14 teams / 1 Division.
My reasoning:
If we begin Season 68 with 14 teams, they can each play each other over the first 13 weeks. We then have single game Semi-Finals for the top 4 teams. Then a single Grand Final for the final 2 teams. This will bring us to 15 weeks and the end of the regular season.
It would be during those last few weeks (The finals - 2 weeks) that we would lock up the League 2 participants and new schedule so that we can begin in League 2 in Season 69.
Thoughts? Problems?
Home Grown; for teams who like a challenge!