@Randomax, I sense a hobbyist nature photographer taking the same kind of journey as me. It's good that you are thinking about your kit as a whole.
As a general observation, I think it takes a little time to settle on preferred focal lengths. You need practice to see a shot as 35mm or 100mm or whatever. One thing about zooms is that they don't encourage you to see the world like that - we tend to frame a shot with the zoom, and hardly even notice what focal length we used (unless it was one end of the range or the other). A prime requires seeing the world differently, and that can take some time - or you might just find that that focal length doesn't suit.
Let's start wide.
If you aren't using the 15 a lot it might be for two reasons. It's not versatile enough, or ultrawide just isn't your cup of tea. I went for an ultrawide because I was constantly using 18mm (the widest FL) on my standard zoom (I chose the DA 12-24 because I wanted greater flexibility than I could get with a prime). If you have given the 15 a good shot and still haven't clicked with it, maybe you just aren't an ultrawide photographer. In which case, strengthen the area you are interested in.
Now, about the 100 macro. What a lens! Macro is just huge fun, but there is more to the 100 than that. At first I didn't use it much as a general tele lens as I found 100 too long or too short, but I'm using it more now. It's my preferred lens for flowers, and when I take the 100 on a walk I am seeing more 100mm shots now. Plus, the lens is so sharp that images can stand a lot of cropping. I went out with the 100 to shoot some flowers a couple of weeks back and got some nice callistemon shots, like this.
Then along came a spinebill to feed from the callistemon, and I got a shot of it acting like a hummingbird.
Of course a longer lens would have been better for this, but the 100 was good enough to take a shot with some cropping.
But, as others have said, both the 15 and the 100 are specialty lenses. Unless you are really confident that one or other of these is a focal length that suits you, to be honest you would be better off passing on both of them (which might mean selling the 15). What others are saying (and I agree) is to get a good wide-normal zoom first (and maybe sell the kit lenses). Those often mentioned are: Sigma 17-70 C, Tamron 17-50 f2.8, Pentax DA 16-85 or DA 18-135. Any of these would pair well with your 55-300. Which is best for you will depend on the trade-off of weight/bulk, price, speed, WR and focal range.
@BrianR makes a good point about trying a Raynox on your 55-300 as a cheap intro to macro, before committing to a specialist macro lens.
As for the suggestion from @ChristianRock to upgrade the body to a K-3 to allow more cropping, well it's kind of what I did. Certainly the 55-300 sings on the K-3 (focus is much better than on the K-30) and the scope for more cropping is handy. But that came after I had developed my kit a bit. Personally with your kit and a limited budget and I would go for a new lens first (unless your budget can stretch to a deal with K-3 plus lens). I think you are some way off pushing the limits of the K-50 yet - it's a fine camera.