Tough one to answer. For header pins, a 40 watt iron is probably fine. If you were trying to do something smaller, I'd say no. The problem you'll run into is you have no temperature control and some pins need more heat than others. For most of the pins, the iron will be plenty hot and you'll need to limit the amount of time you heat the connection. Some of the ground pins have large contact to the ground traces and soak up the heat and you'll need to heat longer to get the solder to flow.
As for reflowing, it may do the trick since most of the traces are on the back of the board. That being said, it is best to remove the solder entirely, clean, and replace it with new solder. The new solder and flux wet much better and flow into the joint better than just heating up what is there. The problem you will run into is System 3-7 pins are tough to remove without a good desoldering tool. A solder sucker doesn't pull out the solder very good and if you have to heat and suck several times, you can lift a trace.
Maybe Hans will chime in. He's the System 3-7 expert.
After all that, I'd say give it a shot. The header pins are more forgiving than a lot of stuff.