It has come to my attention that the following question was put on hold as being too broad: Is there a reliable chemical theory that predicts pKa based on structure?
While I initially commented that there are no rigorous and affordable theories or approximations available, I think that the question in itself is answerable with just that information. Furthermore, it is easy to summarise the current state of research, given in the paper referred to by theorist in a comment, as an answer.
I personally think this is a research level question, going far beyond the +/-I/M counting schemes that are employed in organic chemistry, even though it appears to be somewhat open ended. But we have allowed such kind of questions in the past, so why should we be changing our stance now?