Sorry, if you can recommend QuickBooks with a straight face you must turn in your geek card right now because you sir, are a menace to your customers.
Quickbooks (and Peachtree/Sage) have a timebomb built in which forces a very pricy upgrade when a transaction/line item limit is hit. This limit is of course NOT disclosed prepurchase. So you are either running some very small operation that has not managed to hit the trigger or you just don't care you are encouraging people to fall into a trap.
And the limit is fairly low, we are starting to worry about it (and Sage is sending monthly notices/sales pitches) to us and we only started using it in 2010. And we are a small public library.
This very news source recounts our esteemed editors recent travails with Quickbooks and lwn.net running into the paywall.
That sort of thing happens too often in the Windows world because the customers there are accustomed to being hosed on a regular basis.
And as for the ease of deployment of Windows vs Linux... I was recently tasked with building a small training lab for Win+Office (we are a public library, we got some grant money to offer the classes) so I have purchased the Windows 7 Resource Kit and am reading it. Why am I hearing the theme song from Gilligan's Island when reading it, seeing myself cast as the Professor building everything from coconuts. Deploying on Linux is something I have down to a science, Windows PE and the Windows deployment tools are like returning to Slackware or something.
My current plan in fact is to mostly ditch the Microsoft tools and use a dual boot Linux install to handle reimaging the Windows side. Rsync is fast, simple and understandable without a total retrain. If rsync can't be made to work it will be back to the stone knives and coconuts.