I thought about a 2x9 setup myself not so long ago. What I wanted was something like a 34/46 or similar, which would give me more than enough options through high & low gearing for my riding style. I'm still undecided though, as I could still use a 3x9 setup and throw on a cheap but light alu granny, just to eliminate the risk of the chain slipping off completely.
The roadie cassette at the back won't make too much difference to the shifting at the front IMO, just smoother changes across the rear cogs.
What I found when riding a 2x9 setup not that long ago was that changing from middle to large chainring at the front is certainly possible, but you may need to take a bit more care when doing so. I had real problems changing when riding over roots, rocks, etc. In other words, the best pickup was done when 'cruising', with minimal tension through the crankset.