First quote: It would work, first group starts battle, additional groups come in stealthed? make a stealth check vs enemies perception. It would work as if you tried to make a stealth check and hide mid combat. Either way your late to the fight and don't get to act till next turn, roll initiative and welcome to the fight.
Current implementation of the game doesn't allow for ambushing party to enter combat simultaneously. And they certainly should be able to. Especially cause, by RAW, if the fight breaks out, everyone rolls initiative.
Your solution to use chaining as a criteria to determine who is in combat is incomplete. Because if you are creating an ambush you most likely split your party to surround the enemy.
Second quote: What are you even talking about, you quoted a example of me explaining how the game is currently for non-ranged characters...yeah
I'm talking about your ability to throw that fireball. Which is dependant on characters in combat to be frozen outside of their turns. The only way to guarantee that Gale would be able to do this is if it is your turn in combat. If it's not your turn, enemies start runing around, notice Gale, and pull him into combat. But if you have high enogh APM you can prevent this. Such behavior would be fine in realtime with pause, but not in a turn-based game.
How to resolve surprise isn't the point of this discussion. Moment at which creatures roll initiative - is. Initiative is rolled when timing of events becomes crucial. End it applies to the whole world. Becouse if you create just a buble with stopped time you have to be shure that no events outside of this bouble can affect things inside. A 5 round combat can take hours to resolve. But the world should only advance for 30 seconds.