It seems to be mostly working as I would expect and it looks like you have the PSU plugIn installed as well. I can see that they are work together so that is good.
What does not look as good as it could is that there is an error being raised related to the PlugIn looking for the Virtual Printer port. This is a plugIn that I generally have installed so maybe there is something to this.
Try installing the Virtual Printer PlugIn and see if you get any better results. You don't need to use it. Just have it installed.
Also looks like you maybe turned on general "debug logging". I would turn that off since its not helpful here.
I did some testing and the reporting of hte Virtual printer Error is a caught error so its not causing any other issues. I will likely change the logging on that to be info instead of Error.
That is all just to say, I don't think it is an issue.
Lets see what you are getting in the SIOControl logs. You will have to enable them at debug level.
In the OctoPrint Settings dialog, you can select the "Logging" section on the left side.
At the lower right side you will see "Logging Levels"
In there "select a logger" Select "octoprint.plugins.siocontrol"
Make sure the level is "DEBUG"
Save this.
Now attempt to connect to the IO Device and test it.
Once you have done that a little, go back into the "logging" settings and at the top there is a list.
You can just download the one named: "octoprint.log" You should compress(zip) it and then and post it here for review.
OK, this has shown me what is happening. The 1.0.6 version of the nano base firmware does not support the last change in the SIOControl PlugIn very well. In that update, I added a command buffer for outgoing commands. The PlugIn requires messaging from the IO Device to indicate it is ready for commands. Nano base only sends the needed command "RR" (read for commands) response just once in 1.0.6 at start up.. It should be sending it on an interval 3x the reporting interval to properly work with the latest version of the PlugIn.