Hey, sorry it took me so long to get back to you, my internet's been on and off!
Okay so for your first question, to make two regions is easy enough if you have the map space - not 100% sure about Emerald or Ruby but I know Fire Red does. As for the badges, actually making 16 badges show up might need ASM. But you could always just have your eight gyms with eight badges and then use other flags for your other eight gyms =)
As for tile inserting, I'm still not great, I had lots of help from someone else to get tiles into my hack. The easiest thing to do I would say is to match the colours of the new tiles you want to the colours that are already in the game, if that makes any sense =P
I hope some of that was helpful! =)