I've had both - a screaming 427 and a hot Coyote. Both with EFI and crank driven multiple coil ignition. Starting and driving is the same. Sound is a little bit different, but not radically different.
Aftermarket EFI's like Sniper, Haltech, and BigStuff work really well. Once tuned properly it's like driving a factory built car. Just turn the key and go. But sometimes getting them tuned is a bit of a trial. If you go that route, spend the money for a good dyno tune.
For general maintenance, I think the Coyote is slightly easier to work on. The spark plugs are MUCH easier to get to. And there's only one belt.
The Coyote does not have a stock provision for a power steering pump. Not a problem, though. It's fairly easy to add from the aftermarket.
As far as cost and difficulty rating, it's a coin toss. So get whichever makes you the happiest. Sounds like it might be the Windsor.