I treat all planes as chess pieces and pick a plane that matches the situation well.  To do this I look at the map and see what would be affective given what flight options available.  For instances, if going to an enemy base pick a plane that is more rugged (ACK survivable) and has better than average speed.  Example: FW190F or P-47x
This can change if we have air superiority over a base of course.  There might be an N1k vulchfest in place.   

Another for instance might be in going against a horde, long engagements will probably get you picked.  So I pick a plane to match the tactics to survive the situation.  Boom and Zoom = survive in this situation many times.  Perhaps a P-51 or 190d
Other times I fly just for pure fun.  To me the funnest thing is shooting down perky planes in average planes.  
