What do you think about the trade off between custodial LN wallet (like stacker.news, you just tip by one press) vs self-custodial, using your own wallet (but much worse experience paying LN invoice for every tip)

I think you described the trade-off perfectly. Ultimately I think users have to decide which trade-offs are worth the trouble and which aren't. As tools continue to evolve the differences might narrow, but I think there will always be some form of this tension b/w UX and custody.