Don't buy Cinches, they're all unnecessarily heavy. And from what I've read on these forums, the Rome Arsenals eat you if you're not ready for them (they are Rome's stiffest binders and very unforgiving). They are definityely not a beginner binding.
I'd say yes, look into Targas and 390s. I can't comment on Flows as I've never tried them.
I can't directly comment on the boards as I've never ridden them, but the Brigade and Anagram are part of K2's low end line. Once you're in black/park territory, you'll probably be out-riding those boards.