This seems like it could go in the Help Thread ( But I could be wrong ). BUT ANYWAYS.
I've heard that you can do that while doing certain tricks to it and everything .... But it might cause problems so you might want to go ahead and stick with GIMP for the time being so you don't run into having any issues since it seems that GIMP works best... As for the smoothing part, you could always try blurring it out using the different brush setting until it comes out to how you like it. ( At least that's what I did in one of my first maps and it didn't come out so jagged.
I'm not really an expert but just throwing something out there, hopefully some other floofs can give ya a helping hand here c:
I don't use either GIMP nor SAI, but I'm sure you could just select your whole image and then copy it over to a grayscale canvas in GIMP. I use Photoshop, and I know that it's similar to GIMP, so I'm assuming there's probably a function that converts RGB to Grayscale...not entirely sure though. Sorry if I wast much of a help!
Yep. There is a way to convert to greyscale on Gimp. It's in the advanced options and you can go from RGB to Greyscale. c: