Hello RK forums, I ve been trying unsuccessfully for a while to play ao old client on my mac, often returning back to my pc for ao and other games … but
I had a breakthrough due to an old post on the old ao forums : 557615-Completely-unsupported-AO-On-Linux-howto/page9&s=81ffa7e3354c19304bf1279493f6b3f1.
At post #163 Lliers posted an invaluable bit of info about changing the registry value of wine on crossover mac to avoid getting a black window on windowed mode.
Mind you in fullscreen the old client was a-okay on crossover since ever, but now I can enjoy the game windowed side by side to twitch/netflix/youtube 
The process was to use the default installation of AO ( xp bottle ) provided by crossover ( can someone try this with winery witn a 5.0 wine ?((free )) and repost? ) add some overide libraries like d3d9/10/11compiler_43 ( not sure if they made any difference) and regedit on the bottle. Lliers post also has still valid links for that and use the values provided in that post and boom AO windowed.
I cant post screenshots yet with wine components- ao launcher settings- login screen and ingame shots but i ill later on
Disclaimer : Not liable for any weirdness including dmges caused and I will try to reply to questions but i am not techsupport so i will do at my time
Thank you for reading and enjoy ao on your mac
The result is on the picture up
Some new screenies with settings follow :
Current bug that i have a blue background that by googling I think its a Offscreen problem due to the registry edit that allows windowed ao, or some sort of crossover for mac issue or mac itself when i feel like it i ll try to use winery for mac to see how that goes… The bug
To avoid some of the blue bleed move the window Top left
You wont be able to see your creds or agg/def or sweet ndGUI buttons so the work around is … logging in for a sec with fullscreen
I am not a coder, I just love ao and i am a puzzle ■■■■■■■■■ 
I use crossover mac 20.0.2 I have no idea what later version can do for ao’s old engine but i d guess not much
EDIT : Proper work around for creds/aggdef bar . Use ndGUI
notum|dovvetech GUI. And make a custom control center with the tool provided ( you will need to delete prefs if its not a clean install )
Good luck and have fun