Association mode still breaks itself in a few areas once you get past 5-7+ seasons.
Things I've noted:
When you schedule weekly practices (not development, thats different) you'll notice that all of your players will have a 1-star trade value rating until the effect of practice wears off.
Bad centers with high potential are overvalued by the CPU. So much so that a team will jump at the chance to give away a legit young player, established vet/cap relief, and a pick for a 2nd round 62 rated 7' with B+ potential score.
They don't manage players well at all. There are 6 teams in my league right now that have all but 3 players asking for trades.
In the past when you had a fantasy draft, the initial player contracts were so jacked that it almost instantly broke the league. Now its the other way around. After the 5th year, teams will break their bank signing guys to the dumbest contracts of all time - past all realism. Once the league gets past year 10, every team other than my own was scraping the hardcap and their were 10 80+ rated players waiting in the FA pool.
The draft day trades are a nice touch, but since you're not able to look at the draft pool when its not your pick, it makes judging when to bite on a trade and when not to. The mock draft layout is buggy as well. For example, if you made a trade during the season with the Raptors for their pick while keeping your own, you'll see the Raptors logo for where your team's logo should be. Sometimes all the team logos will be missing. The big board is missing during the draft sim as well. Another thing is that teams will just flatout ask you for stupid trades. "We'll give you the #7 pick for the #4! Derp". It gets annoying. Sometimes there are some good deals that make a lot of sense, other times a team will ask you for 2 first round picks for their second round selection.
The white house visit... cute, but totalitarian overlord-king obama is starting to frighten me now that its 2017 in my league.
BIG BIG BIG bug - Lets say that because of playing time issues, you want to stash your good point guard in the d-league for the season. Okay. Cool. You roll through the season but because of depth issues, you need to sign another center. This move puts you back 15 total players on the roster. If you finish the season with all 15 players, you will not be able to call your d-league player back up at season's end. He will stay there. FOREVER.
Development drills are a lie. Defensive drills will never increase your speed or quickness. Shooting will never improve your 3pt shot. FT shooting can only be improved in the offseason camps. Ball security, offhand dribbling, inside scoring, low post scoring can not be improved at all. Ever.
Tendencies don't change. It doesn't matter how much you develop some guys. They can have a 96 rating - they may never average more than 16ppg.
Another big bug - if you're just thinking of firing your assistant coach, scout, prospect scout or trainer THINK before you actually select fire. Once you select fire, there is no going back. You will be essentially forced to select a new staff member at the next screen because it won't let you back out until you do. This doesn't apply to head coaches though at least.
Homecourt advantage in the playoffs is serious business. I've noticed waaay too many series going on where teams never won on the road. Teams that were obviously better across the board will get pushed to 7 games simply because the road dynamic in the playoffs is just too much to fuck with. If you're simming playoff games, you have homecourt and its game 7 - 9 times out of 10 you will win. Not bullshitting you. Unless someone goes down with an injury in game 7, you're victory is all but guaranteed.
Prospect scouting... its bugged. If your scouts check a guy more than 5 times or more, you'll get a jumbled mess when you try and read their reports. The overall grades and league comparison will still be there, but the reports regarding draft position will be unreadable.
Another issue with automated prospect scouting is that the scouts won't scout to a traded picks likely position. I went on a tear for a couple of 60+ wins seasons and it was very frustrating to see at the end of the year that my scouts had spent all their time checking out players who were mostly in the mid-late 1st/2nd round area instead of in the lottery - even though I had traded up for lottery picks ahead of time.
I don't play with player chemistry usually, but I'll try that when I start a new association mode.