Situation 1: Dola in her airship, Tiger Moth, against Toph on the ground. Dola's airship seems to be fairly resilient and has some powerful guns so I think Toph would need some hard rocky terrain to have enough ammo and protection to win but even then might not be able to. If the terrain is soft earth, clay, mud, etc. then I think Toph stands even less of a chance. But this does feel like too much of a mismatch to allow the airship. But I will give the advantage to Dola in this situation.
Situation 2: Dola on a Flaptor, a one man flying vehicle, against Toph on the ground. A Flaptor is fast and fairly durable but not as durable as the airship. I'm not sure if it even has any weapons. It has a smokescreen but that's pretty useless against Toph. So it can help Dola move around but doesn't seem to add much offensive capability and there is the possibility that Toph could metalbend it to use against Dola. But it might move too fast for her to do that. What I said about terrain for the airship also applies here. But I think I'm going to give the slight edge to Dola in this situation.
Situation 3: Dola in her car against Toph, both on the ground. Dola's car is fast and durable but I think it's a big liability. I think Toph will be able to hear and feel it coming from a long way away. I assume that the car will need either firm ground or solid rock (or pavement) in order to be able to move. If Dola was using the car to keep her distance and not driving too predictably then she could maybe avoid Toph's attacks and take enough potshots to put Toph down. But Toph could maybe use her earthbending to tear up the ground and make it impossible for Dola to maneuver or could use metalbending to just use the car to restrain Dola. I'm giving a slight edge to Toph on this situation.
Situation 4: Both contestants on foot, on the ground. I think in order to win this Dola would have to surprise Toph with her initial tear gas attack and then follow up with an immediate finishing blow to win the match. I don't know if her greed would let her do that or not. Hard terrain would give Toph more offensive and defensive power but softer ground could be used to trip and trap Dola. I think Toph has the edge in this situation.
So since Dola is a representative of air I think situation 2 is going to have to be how this matchup is allowed to take place and so I think Dola will manage to come out victorious (but probably not without some dings on her and her Flaptor).
Situation 2: Dola on a Flaptor, a one man flying vehicle, against Toph on the ground. A Flaptor is fast and fairly durable but not as durable as the airship. I'm not sure if it even has any weapons. It has a smokescreen but that's pretty useless against Toph. So it can help Dola move around but doesn't seem to add much offensive capability and there is the possibility that Toph could metalbend it to use against Dola. But it might move too fast for her to do that. What I said about terrain for the airship also applies here. But I think I'm going to give the slight edge to Dola in this situation.
Situation 3: Dola in her car against Toph, both on the ground. Dola's car is fast and durable but I think it's a big liability. I think Toph will be able to hear and feel it coming from a long way away. I assume that the car will need either firm ground or solid rock (or pavement) in order to be able to move. If Dola was using the car to keep her distance and not driving too predictably then she could maybe avoid Toph's attacks and take enough potshots to put Toph down. But Toph could maybe use her earthbending to tear up the ground and make it impossible for Dola to maneuver or could use metalbending to just use the car to restrain Dola. I'm giving a slight edge to Toph on this situation.
Situation 4: Both contestants on foot, on the ground. I think in order to win this Dola would have to surprise Toph with her initial tear gas attack and then follow up with an immediate finishing blow to win the match. I don't know if her greed would let her do that or not. Hard terrain would give Toph more offensive and defensive power but softer ground could be used to trip and trap Dola. I think Toph has the edge in this situation.
So since Dola is a representative of air I think situation 2 is going to have to be how this matchup is allowed to take place and so I think Dola will manage to come out victorious (but probably not without some dings on her and her Flaptor).