Hi, Valerin! I'm glad you were able to run LOTRO using the instructions in this thread. And I'm sorry you've run in a problem after taking a break. Let's see if we can fix you up.
First, be aware that you can directly run LotroLauncher.exe (the LOTRO Launcher application) but you can't directly run lotroclient.exe (the 32-bit client application) or lotroclient64.exe (the 64-bit client application), they must be invoked by the LOTRO Launcher application. This isn't some limitation of WINE, the clients are designed to work that way, they won't launch without the parameters sent to them by the LOTRO Launcher application which transmits your credential authorization and server choice, among other things.
When the "Where is the game executable?" dialogue appears, that usually indicates that you are attempting to run the 64-bit client in an environment which lacks the resources to run it. The most common cause is a version of WINE which supports the running of only 32-bit applications. However, your UserPreferences.ini file includes the line GameClientType=1 which is the 32-bit client.
I'd like to see the rest of your UserPreferences.ini file (with your account information redacted to protect your privacy). For example, I'd like to confirm the version of DirectX set in that file by examining the expected line GraphicsCore=D3D9.
I suggest disabling or uninstalling CleanMyMac, at least while performing the troubleshooting related to this problem you're experiencing with LOTRO. You can enable it or reinstall it afterward.
You can determine the version of WINE on your system by running this simple Terminal command:
Also, look in your /Applications folder. You should see an application called Wine Stable, Wine Devel, or Wine Staging.
In your next reply, let's see your full UserPreferences.ini file (again, minus your account name and any other personal details), the output of that Terminal command, and the exact name of the Wine X application in your /Applications folder. You can also try this before replying:
1- Edit your UserPreferences.ini file so that GameClientType=3 and GraphicsCore=D3D9 if necessary.
2- Open a Terminal window. Type the following into your Terminal window, without the quotation marks:"wine "
Be sure to include a single space after the word "wine".
3- Using the Finder, navigate to ~/.wine/drive_c/Program Files (x86)/StandingStoneGames/The Lord of the Rings Online/LotroLauncher.exe and drag the LotroLauncher.exe file into your Terminal window. Doing so will populate that window with the exact file path to the LotroLauncher.exe file.
4- Hit the RETURN key on your keyboard to run that command line.
5- The game ought to run. If it does, great! If not, report back with as much detail as possible.