What happens, when after you submit your userid and password via "logon" in Pylotro.
You should get a Turbine Logo (swirlie thing with sound)
You should get a "splash screen" an add for DDO
You should then get a "searching screen" quickly followed by a "loading screen and status bar.
Lastly as the status bar completes, you should be on the Character selection/creation screen and the music begins playing.
As I recall, when DDO fails, it will generate dumps and logs in 2 or 3 locations.
If I remember correctly...
One is in the ~/Documents/Dungeons and Dragons Online/ ... this is where your ddo.keymap file and UserPreferences.ini
files live (or should live) as well as any screen shots you might make later.
Anther location is
~/Library/Application Support/CrossOver Games/Bottles/<yours>/drive_c/users/crossover/Application Data/Turbine/
And finally (and this is probably the meaningful/useful one)
~/Library/Application Support/CrossOver Games/Bottles/<yours>/drive_c/Program Files/Turbine/DDO Unlimited/
In this last directory, you may find a file "dndclient.log" which may or may not have anything useful in it.
If the client is actually crashing, it will say so here. If it is just hanging, it won't say anything useful.