Answers based on my experiences.
A) For $50 you can buy a Rolls Personal Monitor Amp. You plug your mic into it and either a headphone or a powered speaker. If you use Etymotic Earbuds, you can use them to partly block out the other noises around you and hear yourself really well.
B) You can only use the same mic for vocals and whistles if you have a way to adjust the volume, because vocals need a lot more gain than whistles (unless you sing really loudly, I guess). There's no reason the soundman can't adjust levels on a song by song basis (but you might need to remind him). If you want to sing and play on the same tune you should use different mics if you don't have a way to switch the response.
C) EQ depends on the mic, the venue, the mix, & the speakers. But aside from resonances (feedback), there's no particular reason why you would need to EQ either the whistle or the vocal.
The standard stage mic is the SM57 or SM58 (basically the same thing). It has a pronounced peak at about 6 kHz. To me, it's not a particularly good mic for whistle. I recently used an SM81 and it worked really well, but it was more susceptible to wind noise from the fipple.
As far as foot pedals there are a variety of possibilities. If you used a mic splitter you could split the signal in two, feed both sides into a small mixer on the stage, then take the unbalanced outputs from the mixer into an A/B footswitch. You could use the EQ and gain settings on the mixer to tailor the two sounds according to your needs.
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