It might be worth giving UTAU a go first to see how you get on with a similair software Vocaloid. UTAU is at least free.
Mostly, it boils down to music experience rather then software experience as you can learn how to use Vocaloid over time. You also need additional software like Reason or FL Studio to take full advantage of Voclaoid as a music software.
It is also recomended to try out the free vocaloid demos on Zero-g's site. While only the demos are only for the Vocaloid 1 software it is easy to get used to the software.