I second that I want to gather information and might ask as a priority question can I find out if any of the the friends and family, or the people who I currently know, are in either society? Can I find out what their reasoning in choosing that society was? How have their interactions been with family members and friends who chose the other society (if any) through the monitored communication lines?
For instance, if the answer is 'Everyone you know is dead and their descendants(if any) don't find an old fogey like you particularly relevant, so none of your above questions grant you any information.', I might pick the the telepathic society, because the loneliness of current society minus all current social contacts seems incredibly depressing.
But there are so many answers I can potentially see to those questions I find it difficult to think of my responses to any particular scenario without narrowing down the question and I'm not sure what I should consider the Unfought Hypothetical baseline.
I asked this question on IRC before and got some surprising answers.
Suppose, for the sake of argument, you get cryo-preserved and eventually wake up as an upload. Maybe meat->sim transfer ends up being much easier than sim->meat or meat->meat, or something. Further suppose that you are not particularly averse to a digital-only existence, at least not enough to specifically prohibit reviving you if this is the only option. Yet further suppose that sim-you is identical to meat-you for all purposes that meat-you cared about (including all your hidden desires and character faults). Let's also preemptively assume that any other attempts to fight this hypothetical have been satisfactorily resolved, just to get this out of the way.
Now, in the "real world", or at least in the simulation level we are at, there is no evidence that telepathy of any kind exists or is even possible. However, in the sim-world there is no technological reason it cannot be implemented in some way, for just thoughts, or just feelings, or both. There is a lot to be said for having this kind of connection between people (or sims). It gets rid of or marginalizes deception, status games, mis-communication-based biases and fallacies. On the other hand, your privacy disappears completely and so do any advantages over others the meat-you might want to retain in the digital world. And what you perceive as your faults are out there for everyone to see and feel.
As a new upload, you are informed that many "people" decided to get integrated into the telepathic society and appear to be happy about it, with few, if any, defections. There is also the group of those who opted out, and it looks basically like your "normal" mundane human society. There is only a limited and strictly monitored interaction between the two worlds to prevent exploitation/manipulation.
Would you choose to get fully integrated or stay as human-like as possible? Feel free to suggest any other alternative (suicide, start a partially integrated society, etc.).
P.S. This topic has been rather extensively covered in science fiction, but I could not find a quality online discussion anywhere.