You're close, but not quite right. The first number on an IMS/OotS is the number of bursts required to use it. I believe most if not all of the demo aircraft have one burst when neutral, two when advantaged, and four when tailing (none have any bursts when disadvantaged or tailed). This can be modified by the Marksman skill, and some of the other aircraft are different. So basically, you can play as many IMS/OotS cards as you have bursts. An uncontested Maneuver will normally give you two bursts (assuming you went from Neutral to Advantaged) and would allow you to play an IMS/OotS 2:X or two 1:X. Playing Maneuvers, Half Loops, and Vertical Rolls against a wingman also gives you more bursts to use, although there is no change in the onscreen graphics in that case. You can see how many burst you have available in the pilot display: its the last line, IIRC.
The Wingmen get a fresh hand of cards (generally two, unless modified by skills or damage) each time they have the change to attack or are attacked. So basically, there is no reason to hold back with Wingmen: any cards left in their hands at the end of the attack sequence are discarded.