Hi Again James,
I don't know if I am going to be helping at this point, but let's see what we can do.
The example that I showed you is from vehicles on our radio network. One of my servers is polling each radio in each vehicle. The packets containing location information (along with velocity and time data) then get sent to our GeoEvent Server installation. In GeoEvent, I send each packet through a process that generates bearing and the categories that you saw (if speed = 0 then GPS_Status = "Stopped"). GeoEvent then writes this to a Feature Class in my enterprise geodatabase. I then create a Web Service from that Feature Class that I place in my Web Map. The Web Map then goes into the Operations Dashboard.
I created the GPS_Status field originally to just display if the GPS receiver was delivering an accurate location. I did not like the fact that I got an arrow pointing North when a vehicle stopped, so I added the "Moving" and "Stopped" categories.
So, I have the option to craft my service - you don't at this moment.
Staying with the categories topic, you can add categories by symbolizing on a field at the Web Map level. That is, if you have the information that you want to symbolize on in a field of the Feature Service. For example:
When the Option button is clicked, you would see the options in my first reply to you. The symbology options can be edited there.
BUT - take it one step further.
Make a copy of your Feature Service in the Web Map.
In that copy, look for the Filter button...
when you click, you get the filter options that allow multiple and/or statements. In my case, I have incoming AVL packets that have not been configured properly, which happens when a brand new radio with a brand new IP address gets fielded. If my "Label" field is empty, I need to know so I can fix the issue. I can use the same feed and a filter to accomplish that. I just use that Feature Service copy with a filter of "Label is blank" and symbolize with the same symbols - but they are yellow instead of white:
I would then go back to the original service and filter it "Label is not blank" so that we don't have both copies showing a symbol for one feature.
If you have an "emergency status" field, you could use this type of copy and filter too. Don't filter out of the original copy, just make a highly visible transparent symbol to appear over the original symbol when emergency is declared....
The reason I brought up the "Add a service" versus "Add layer from Web" is because I have had different odd behaviors from the Add Service/search method. If you go to the service description, it should display the REST endpoint link that you can manually add to the Web Map through the "Add layer from Web" method.
Next topic: Operations Dashboard for ArcGIS. When you say that you use "Operations Dashboard" (NOT Beta), I am assuming that you are using the downloadable version to view the map? If so, you may want to also try the web-app version. Go to the Operations Dashboard item in your AGOL and click the little arrow next to the "Open" link and select the one that says (Browser).
It isn't the same nice environment, but it may isolate the problem to the Windows application.
Be aware that the other version of the OD is the Beta version - the eventual replacement for the current OD. It is not complete yet. You will not have certain options that you now have until it is complete.
If this doesn't get you to where you want to be, we should talk on the phone. Just ArcGIS Desktop is not going to be enough. Drop me your number in a PM and we can talk.
--Adam