What's up man,
What I would do to help answer you question first is take a look art some YouTubers, I would prolly start in 2k23 as that can answer a few questions as you play it.
If you start in Jordan era, you can I believe play through 80 years from that. As you cycle through the years, logos change and floors and jerseys.
Players retire dynamically. if they do well and are killing it, they continue to play until like 18 years. If they aren't playing well and are wack, they retire.
You can also put off retirements but again I must say that this is not 1:1 of real life. MJ can retire at any time... he retired in 1999 in 2k24 and in 2k25 he is still playing for me
Draft classes have a good amount of LICENSED players per class. Now you have a lot of custom user draft classes created by many that will give you all the the real names and information via 2kShare. Those people truly are GOATs.
For more information on ERAs take a look here:
https://nba.2k.com/2k23/courtside-re...idereportaug18
Hopefully this helps