Issue with auto load yearly logos, uniforms, hats

[RyMACtizzle]

I tried this on Bug Thread and got no replies, so I'm trying it here.

I have a fictional league that started in 1900, and have made logos, jerseys, caps that change every 20 years or so for every team. It is now January 1st, 1920 and many teams should be changing logos, jerseys, etc.

I simmed to preseason and it looks like the primary logos changed, some of the secondary logos loaded incorrectly (loaded 1980 versus 1920 small logo), and no uniforms for 1920 loaded. Simmed a couple of games into regular season and no 1920 uniforms.

Here is my info:

OSX version (not App store)
Build 19.6.53
Downloaded files to FTP site
5 leagues of 20, 10, 16, 8, 8 teams and a minor league affiliation with 20 teams.

Sample files:
manitoba_buffaloes_1920-1929_1c5382_ffffff.png
manitoba_buffaloes_1920-1929_small.png
caps_manitoba_buffaloes_1920-1939.png
jerseys_manitoba_buffaloes_1920-1939.png

I tried it with just the 1920 and not 1920-1929, still no auto-load on jerseys or hats.

However, unless I go individually to each team and hit auto-load for jerseys and hats won't update from year to year. I even tried the Load Game and checked the check for logos box. I tried to reset team logos in Game Settings screen also. So, my naming convention is correct, they are stored in correct place, and they auto-load with correct png's for that year when I go individually. Eventually I'll probably have around 500 teams in my universe with different logos, jerseys and hats for different years and individually auto-loading each team is not really an option.

My questions are:

1) When do the logos (preseason?), uniforms, hats change over from year to year automatically (or do they in a fictional league?)

2) Is there some reason it doesn't work on Fictional Leagues correctly?

3) Can somebody please help me, if I am doing something wrong?

4) Has anyone else ran into this issue?