I've used both money and quicken, in many of their annual guises.
For starters, be prepared to buy the new one every year. Good news is you can usually get it for free or nearly free through moderately simple bundling/coupon/rebate scenario's via one of the many office supply stores.
Next, a lot of work up front to get everything in there, and then a fair amount of time spent making sure everything gets regularly synchronized properly.
After that, finding and correcting many little glitches. For example, ameritrade downloads some information to quicken incorrectly, and after several years of haunting them about it and them promising to fix it and not doing so, I quit using ameritrade.
After that, you can in fact funnel the info into turbotax, but be sure to read every line of every form produced, as my ameritrade to quicken to turbotax combo produced a schedule "D" once that the IRS was highly interested in and wanted to ask me lots of questions about. Turned out to be nothing more than a re-write of that form and no taxes or penalties, but that wasnt one of my favorite couple of weeks.
I'm pretty happy at this time doing all my investing through vanguard, and all my banking at the same place I've been with for 25 years. At the end of the year I'll use the free vanguard turbotax for the web tool, type in a couple of 1099's I'll get, all my deductions, and being done with taxes in an hour or two, minus buying any software, building my life into financial s/w, or proofreading anything to make sure some piece of s/w didnt screw me up.
But some people live in quicken/money and cant get by a day without firing up a graph of their monthly fish fly usage broken out by type and cost bands.
