I would think after the initial install was complete and before doing any other config changes.
I’ve gotta logoff for the day but will check by in the morning and wish both of you the best of luck.
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yes it worked. the error is gone. That is the workaround. Right after installation over ethernet, do the raspian-config for wifi (not the openhabian-config). Here the link to the post of the guy who did it first https://github.com/openhab/openhabian/issues/378#issuecomment-449870571
@H102 Thank you very much! Without you I would have not made it. 
I can sleep now
Glad it worked.
@Nico111 after a fresh install, did logging in and using sudo raspi-config to set Network SSID, Passphrase, and WiFi Country then a reboot work for you as well?
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That’s actually what I did when reinstalling OH on the SSD.
I’ve left all preconfigurations away as well as the openhabian-config wlan configuration and only raspi-configed into my wireless network.
Didn’t worked after a reboot but can’t really tell since it’s now in my network room and connected via ethernet, it’s way better anyway hehe
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I agree with using Ethernet whenever possible.
Hopefully @VioletAnt is still running OH wireless and without issues.
If so I would say this topic can be marked as solved and the solution is to use sudo raspi-config to set SSID, passphrase and country then reboot prior to any other configuration.
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The cause of the problem appears to relate to the creation of the /etc/network/interfaces file when the wifi system is enabled. the dhcp daemon doesn’t like the entries in that file and refuses to start. Commenting out the wifi entries allows the dhcp to start, either manually or by reboot. The system then gets an IP address and can be accessed via ssh.
The sudo raspi-config solution does not work in the current OH2 as it has been deleted from the distribution.