I think that it depends on your ears. If you can have a top of the line analog, with effects, a great EQ and 12 tracks, or the first price digital one with 8 of them, without effects, well, I'd go with the analog... DUh...

Actually, you have to know that you need to KNOW your equipment. Some pros only own a strat and a fender amp, and they can sueeze every tone you can think of out of this setup. One example is Dany GATTON. The guy had a telecaster, an amp, and If I'm right, he shared the slapback echo effect with his singer... And dude, everything came out of this setup... Wah wah sounds, dive bombs, pedal steel licks, rockabilly tone, Jazz licks, Rock and Roll, Country etc...
So don't worry if your setup isn't quite the thing you want, because you can't afford it. Try to squeeze everything out of your setup, and then some.