I have struggled with Quicken (currently Q07) for many, many years (back into the 90's). I'm still using Quicken Home & Business on an aging pc (sigh, just upgraded to Quicken H&B 2012) because there is nothing even remotely comparable to it on Macs. reports are very basic with very limited customization. tax category support is useless to nearly non-existent. there seems to be more emphasis on having a pretty UI than on capabilities. Even though they are the best of the lot, they still have a long way to go to be truly useful.
Last month I installed iBank and Moneydance on my Mac to evaluate the current versions of each. But if you want to do meaningful recordkeeping and reporting, print checks, tax categorization, etc. If all you want to do is keep a transaction register, almost any of the apps will suffice. That said, you might start by checking out Mac Personal Finance Software Reviews everyone wants it, but no one can find it. So far, good financial software for Macs is like the holy grail.
