Hello Jonathan,
the questions are not dumb, don't worry. I can speak for myself. I can play the tunes by heart, those 50 and switching between songs and rhythms comes easier with practice. When I was younger and I had more spare time I listened for hours to old recordings, now I don't have that much time.
For me personally the important thing is not how many songs can you play but understanding the essence, the base characteristics of the Rhodope music and kaba-bagpipe playing.
So it is important to listen not only to bagpipes but also to singing. In time you will get used to the music and reproduce it with ease.
Technically the kaba-bagpipe doesn't require more time than the other instruments. One can follow the paved rout starting with plain melodies note by note and gradually adding ornaments which have very sound logic and hierarchy and be a bagpiper who can play for audiance in 4 years. So don't despair.The problem is that as for now there is too little information and help available outside Bulgaria. We try to change this.
The difficult but also the most pleasant part comes after those four years when you have gathered some experience and you are able to understand and interprit the old masters.Then you begin to build an own , unique style and that takes a lifetime :)
I would advise you not to hurry and to practice. Not a long time ago I spoke with a friend who has learned the bagpipe for almost 2 years and said to him : "did you remember that the previous year you didn't believe that you could play the things you can play now" and he realized what a great progress he has done in only 6 months.
Greetings,
Kostadin