I agree that using the grid, particularly in tight situations, is probably the way to go. And I agree that not using the grid puts a burden on the GM. But only because that's how the rules are written. Players know this, and when you don't use the exact miniature rules, they naturally protest, and they are right. If you want to role-play on a different level, some major changes have to be made. Don't get me wrong, I am not saying using miniatures or strict miniature grid rules, totally invalidates your role-playing. It is fun playing with miniature rules with role-playing thrown in, I've done a lot of it. "The Fantasy Trip" had this developed quite nicely. Conan RPG has a better miniature rules set, IMO. So I think you can't go wrong there. But, and it's a quantitative but, moving to a flowing dynamic combat system that only uses miniatures for initial and final placement, is the way I believe role-playing needs to go. That's my opinion and feeling on the matter.
Let's take a look at the flanking aspect of miniature rules as I now understand it with Conan RPG. Only combatants, on opposite sides of the character, may get the flanking bonus. This may be figured from an eight-sided square as being from corner to opposite corner, from side to opposite side, from side to opposite corner and vise versa. Squares directly diagonal or adjoined to the side of the attacker are not considered squares that are opposite, naturally. Makes clear as to whom can flank. Also, flanking is only possible if your character is in melee also. Thus, this leaves out missile fire.
Dynamically, the flank of any combatant is his side or back (making a back "stab" is only possible in surprise attacks). This will change rapidly, a simple reflex can turn a character in fractions of a second (remember, one of the world's fastest men, can draw a pistol and shoot at a target in 1/3 of a second!). If you are attempting to make a flank attack, you will have to "Outflank" the opponent. This, of course, relies on you having the opponent distracted by another ally. This does not mean you will necessarily be on the exact "flank" of the opponent. Again, your character will be constantly moving, dodging, parrying, and what have you, just as explained in many of the early D&D treaties on combat. The attack you actually strike with is but one of many you attempted. But your overall objective is to get a blow to the unprotected side of the opponent, not just to beat down his guard and pierce him through. So you declare as an "Action" that you are attempting to "Outflank" your opponent. You must check your "movement" skill against the opponents "movement" skill, and if you succeed, you may then attempt to strike the opponent, but you get to add the flanking bonus. Consider this also, the "movement" skill of the opponent can be limited by terrain (includes walls) and other attackers. You will find that "skills" become very useful in the game. You will begin to make skill checks more often, and stop depending on your skill to move to the right square on a map. So how do you get into a "position" to Outflank a character? At the beginning of your "Positioning" you simply tell the GM that you are going to "Engage" the opponent, and this places your character next to the opponent. If you are using miniatures, simply touching bases works or placing the miniature in a square close to the opponent as you would normally do, works. Actually, "winning" the "position" becomes part of the initiative round. Depending on your surroundings, you might want to be first to get into position or last to engage.
I know this is radically different, and most likely not be of interest to many gamers. But I guarantee, once you and your players start using this regularly, you will find the flow of the game very fast. I have been testing this out on several RPGs, and it's going quite well so far. The only game that uses a system similar to this, and actually is where I "borrowed" the idea from, is Paranoia. Of course, with Paranoia, positioning as such, is totally arbitrary.
This is just an idea, and has not been tested by anyone else but me, that I know of. But I'm having fun with it, and just wanted to share my idea.