My understanding is that the Deen adaptations of Higurashi and Umineko both suffer from the effect of squishing large works in the time given by a show, though the Higurashi one handles that much better and still gives a good experience, even if a big part of Higurashi in my opinion is what you get from a first person perspective. At the same time, the Deen Higurashi works as a slimed down and less time consuming experience. Plus, the Higurashi VN does have some bloat that the sped up experience of the anime helps with.
So, the Deen Higurashi anime might be the most accessible option. I feel that the VNs are the better experience, but both Higurashi and Umineko take time to go through and Umineko is a huge read. So, the old Higurashi will work as a starting point, with the option to go to the VN if it interests you.
Also, none of the three When They Cry stories (Higurashi, Umineko, Ciconia) have connecting main stories or do more than references in regards to each other. That means that any can be picked to read without needing to know what happened in the others. I would say though that the bit of Ciconia that is out might be easier to read once you've read at least one of the other WTC works. So, probably better to avoid that one as a starting point.
