Keep asking the questions! They've resulted in a some really interesting discussion. I've been reading woodwork books and magazines, and butchering bits of wood (in a very amateurish fashion), for the best part of thirty years, and I've still learned allsorts from questions like these.
How often to sharpen a saw? Ah - well - that's a bit of a 'how long is a piece of string' question. Aside from the trite (and rather unhelpful) 'as often as it needs it', there are so many variables that there isn't a sensible average time interval. In the book, 'The Tool Chest of Benjamin Seaton', there is a passage suggesting that saws needed sharpening twice a week - but these were being used by craftsmen working an 80-hour week, and having no access to machinery - their saws got a LOT of use. At the other end of the scale, I suspect that most of us amateurs have saws that have done some years between sharpenings - especially the ones that don't get much regular use.
One indicator that might help is to turn a saw teeth up, and very lightly pass a finger end or the ball of a thumb along the tips of the teeth. If they snag the skin lightly, or catch, the teeth are sharp. If the skin slides easily over the tooth tips, the saw would benefit from a touch-up with a file. Take a look at the tips, too. A gleam of light on each toothtip indicates a polish that suggests the edge has been worn off - no gleam of light indicates no surface on the tip to reflect light, and therefore a sharp tip.