Issues with rebooting on hassio running on debian 9

I have hassio installed on debian 9 and for some reason everytime i try to reboot hasiso from any place (general -> restart / SSH -> hassio ha restart / ho reboot / VM Host shutdown -r now) it takes 3-5 times for me to reboot it for it to load completely.

The log for homeassistant doesn’t really say anything. first reboot the web ui never returns. the SSH addon and the Configurator addon are still up.

The log shows the following:

2018-12-10 08:19:39 ERROR (SyncWorker_44) [locationsharinglib.Service] Could not open pickle file, either file does not exist or no read access.
2018-12-10 08:19:46 WARNING (MainThread) [homeassistant.setup] Setup of zha is taking over 10 seconds.

I also have issues updating the hassio instance whenever there is a new release. I can provide any info needed to help me out. i am also not against trying other methods to get this running stable.

Thanks in advance