I'm a novice and i learned quite easily. Coming from something 100% hardware-based like an acoustic piano, electronic piano, synthesizer or workstation keyboard, the biggest leap is accepting that when you buy-into the VST world, everything is computer-based. So at the absolute minumum, you've got your controller switched on, a computer switched on, some software running, and usually some kind of powered speakers plugged into your computer's headphone sockets or plugged into an external USB audio interface. So it's nowhere near as streamlined or elegant. And you have to find a place for all this gear to sit. And there are wires everywhere.
But, the flexibility and potential, completely smashes what can be achieved with just one master workstation keyboard. When you start using digital recording software like Ableton, Logic or even GarageBand, there's nothing you can't do, from just simply recording what you play in one take, to compiling huge multitracked professional productions.
Speakers? Presonus Eris 3.5 at under 100 £/$/€ make a great first pair of powered monitors. Comparatively small and unobtrusive, they are better than most speakers built into digital pianos or workstations.
