I'm a newbie but I've begun my tarp journey. I started with the stock Hennessey and still think the HH is a perfect all round starting point (zip model). I finally bought a Warbonnet Edge because I got to thinking what it would be like to be holed up in my hammock for an afternoon. I knew I could hang the stock HH tarp tight over the top and stay dry but then I'd be stuck. I chose the "Edge" tarp so I'd have some room under the tarp if the rain was coming straight down so I could sit under the tarp and enjoy it.
I'm thinking of one more tarp, the Warbonnet Mamajamba (sp?). It's even larger and has a door kit so it would work well for spending a few days in one spot and for winter hiking.
But beyond that I can't see the value of cuben unless you're really going over the top for ultra-light. I am going for lightweight but I think even the Edge is really all you need.
It's easy to get caught up in it and spend too much time and money fretting over the gear. I enjoy researching and buying gear but if you can't be satisfied and enjoy the setup then it's defeating the purpose in my opinion.
So relax and hang but I think a decent mid-size lightweigh tarp is the best of all worlds.