Those look like bigger changes than I expected.
Let me comment on the new features as I'm not in the focus group.
Design - I think the current design is nice and modern, the new one looks obviously great, but maybe it was not needed to put the time into making new design.
New league system - both increased number of teams and new playoff format sound great I think this was needed a lot. Looks like a good balance. Now its time to get as many human manager as possible, as world with less than 50% of human managers will be, on some levels, boring as hell...
Inbox/Messaging - yes, that was already a must even before the new update. You really should make it for the fall update!
New database - this sounds also great! As are other features like jersey editor or tweaks to player development and potential.
Relaunch - I think it is sad to restart the worlds completely, but I understand it has to be done as the database would not work and old teams might cause a lot of problems. I like the options to offer moving team name, colors, manager history record to the same league level of the same speed world after relaunch - how this will be done? You will send a message (email?) and wait one week for answer to do it for the user manually or this will done automatically by user when he first time logs in into new game?
Business - Yes, I completely agree this game needs to go to green numbers and pay you for the hours you spent developing it.
Shaka Productions - I have tried to google it and nothing relevant came up. Weird? What I mean is that this game needs is a big promotion - articles in hockey related sites and so on. or partnering with a big player in the field. Partnering with friend is obviously ok, but for a real business I think you need even a bigger step...
pay to win - I'm with you, this can never be a pay-to-win game. But on the other hand I think this game should still offer free playing. I think that all star account is good way how to make money - you just need to expand to have thousands of users instead hundreds, which will make hundreds of paying users instead tens of them...
I will obviously pay as I really like this game and 3.50$/month sounds reasonable to me, but on the other hand I can see large % (like ~50%) of current users not paying that and quitting, which will still give you more money than current all-stars, but it will leave the worlds half-empty and boring on lower levels, so boring for newcommers and thus very few new users that will stay after the free trial. I hope I'm wrong, but I see that as this will mean an end to this game. I'm not kidding about this.
30 days free trial is not enough for slow worlds - with 80 games per regular season and 5 games playoff series, the 30 days is not even 1/3 of the season.
Anyway, it is your decision to go this way and I understand, but in that case I can't say it louder - YOU NEED MORE USERS to keep the leagues full and the game alive (plus it will bring you more money to possibly do this full-time). You need to promote the game at various places, sites that writes about NHL or about hockey fantasy.