Is it possible to add more than one shortcuts portlet to a dashboard? Like if one gets crowded or I want to have multiple so that I can group short cuts according to two different types to make them easier to find

Look into the Navigation Portlet SuiteApp

Or just create a custom portlet and include whatever HTML you like. I have something similar which adds in Font Awesome, so you get nice big visual icons instead of plain links, which makes it a lot more intuitive.

You can also create a custom Tab with links to anywhere you want and apply it to an audience e.g. role(s)

Interesting... It would be nice to see what these new portlets look like, but i'll just install on my sandbox and see