It sounds like the core of your issues is that you want a richer way to display content in the static part of the timeline to the right of the clock. You have a couple of options.
GDK
If you'd like to stay pure GDK, you can create your own view, and flatten it into a bitmap. The steps to complete this are the same as for other Android devices.
Mirror API
You could also use the Mirror API to insert HTML static cards using timeline's insert method, but to do this you will need to communicate some authentication information to your GDK Glassware. For example, if you want to insert into the Mirror API directly from Glass, you would need a way to provide an access and refresh token to your GDK Glassware.
There is no graceful way to do this with the released APIs, but I've seen some people accomplish this using the OAuth 2.0 flow for devices or scannable QR codes.
If you go down this route, be prepared to update your implementation. Google has announced improved support for sending authentication information to GDK Glassware. Once it's available you will want to switch over to it.