Earlier quoted context omitted.
I've probably read a hundred or so pages on my own, and 'recaps' by Russel, Durant, and have spoken with practicing philosophers about him. I have enough exposure that I've been able to make much more sense of why later philosophers seem obsessed about certain points that only make sense if you consider the historical philosophical tradition from Plato. But hearing people talk about him, especially when they insist o…
It's not about the answers, but about thinking deeply about these questions and questioning your own assumptions (and those of others). I'd highly recommend taking an intro to philosophy course, or one on ancient philosophy, where you can read the Socratic dialogues and engage with them in a group setting, along with others who are encountering these for the first time. When done well, if you're lucky enough to have…
I see what you mean about doing philosophy in a group setting, but for what I'm interested in anyway, I'm not going to have a great time debating the above questions with an intro to philosophy class. A starting point for me to enjoy it would be that my interlocutors would need to be able to have some degree of understanding of the answers I gave above, what points might be in their favor, and what their limitations might be.
I can say no philosopher I've met personally would answer those questions like I did (though I think I've read some who would), so I'm still very curious to see why we choose different ways. But my guess is still just that they'd answer differently if they had more knowledge of cognitive science and other topics.