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Well, raw waveforms aren't so difficult to make, it's not that that will make a digital synth sound different from an analog one.
The only real difference here will be in the type of waveforms used.
What one manufacturer calls a square wave, won't be the same square wave as with another manufacturer.
Someone here mentionned the slopes for one kind of square waves aren't right, but slightly angled. Well, a perfect square wave only exists theoretically (square wave means : one fundamental frequency, with only odd harmonics, stretching to infinity). Practically, you'll only come close to a square wave, as infinity isn't possible up to now. If you filter down (lowpass) a square wave, ultimately you'll end up with a sine wave of the fundamental frequency.
Now the thing is, if brand A uses a square wave that comes close to theoretical limits, but brand B uses a less well constructed one (more rounded, so less harmonics). The second still resembles to a square wave from far, but will definately sound different from the first. But both brands will call it square waves. I only give the square waves as an example, it can be any type of waveform. If the first one decides to make a saw with a gentle slope, while the other one decides to give it a tighter one, well they will sound different.
But, like I said, making waveforms is not the biggest of concerns. Usually (not always), software and VA synths don't make their waveforms out of scratch but start from sampled waveforms, unlike real analog synths. So, in "digital" synths, it's not really a question of analog vs digital sounding waveforms, but more of what waveforms the manufacturer used (they decide which exact waveform will represent square, or saw, or whatever).
In real analog oscillators, there will be imperfections, and it's those you can hear as "analog".
But the biggest difference will be in the filters indeed. Analog filters have flaws, even the best (very expensive, but those are generally not used in synths) ones. But it's just those flaws we learned to like as the "analog" sound. You can emulate such filters in the digital domain, but it will remain an emulation. You need lot's of processing power to emulate something well. Usually in software form some compromises have been made, so you don't bring the cpu on it's knees just playing one thing. VA synths usually also have digital filters, but have dedicated processing power to make the calculations, so the emulation will usually be closer. Compared to real analogue filters (take the famous moog 4 pole filter for example) there still will be a big difference.
If a digital filter sounds analog, it either means it will eat a lot of cpu to achieve this, or the programmers have done an excellent job at cutting corners while retaining a psychoaccoustically close emulation.
Of course it would be silly to claim the only difference are the filters. Internal processing can also affect the sound, and so do the input/output convertors. But waveforms, in my opinion that's not really the biggest concern, as even imperfect waveforms are pretty easy to recreate with today's technology.
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