It would probably help if you said a little more about what you're interested in specifically in philosophy. What kinds of questions grab you? Philosophy is a pretty diverse discipline in terms of topic (it's not clear to me what the metaphysics of grounding and the ideal form of the state have to do with each other), and trying to slog through stuff that you aren't interested in will probably result in your abandoning the project.

If you want something introductory, I'm told that Bertrand Russell's "The Problems of Philosophy" is pretty good. You may also want to consider finding a recording of a philosophy class on a topic you are interested in somewhere, since that kind of material is pitched at a student rather than an expert.

I also really don't think it's at all necessary or even desirable to go in temporal order. I'm pretty sure most professional philosophers have not read all important historical figures, and certainly not in order. Plus, a lot of historical texts are going to be very difficult to understand without guidance from an expert--I mean, even experts have deep disagreements about how to understand most philosophical texts, and I highly doubt a beginner is going to be able to make anything of Aristotle's Metaphysics or Kant's Critique of Pure Reason. No matter how smart you are, that stuff is tough.

I don't think it's quite that simple. I think there are naturalistic views about the relation between the mind and the brain (ie. the mind isn't made out to be a separate, often spooky, substance or property) that can allow for the possibility of mind "transfer" from biological bodies to electronic ones. Specifically, seems to me that you could think that mental states supervene on physical states (ie. there's no change in mental state without a corresponding change in physical state) and that the mind is not a separate substance from the brain, and still think that it's possible to "pass" a mind from one physical medium to a different one. There's an idea in the philosophy of mind (and probably related fields as well) called "multiple realizability" which basically states that the same mental state can be realized in multiple physical ways. So for example, if the idea is true, then my present mental state could be a result of the firing of neurons (as it actually is), but it could also result from, say, the passing of currents in a circuit (if the physics is in fact amenable). Now we know that minds can be "passed" from the one arrangement of atoms in the human form to another (the atoms in your body are replaced as you age, but you presumably retain the same mind, at least if skeptical arguments against personal identity over time don't hold), so given that the relevant mental states can be realized in some other form, I don't see any reason in principle why it would be impossible to pass a mind from a human form to an electronic one. I mean, there are still a bunch issues regarding personal identity in play here, but I'm not sure they aren't issues for any naturalistic view of the mind at all, regardless of whether it would be possible on that view to pass minds from brains to other mediums.

The intelligibility of this entire issue may turn on a dubious understanding of what a mind is though (I'm personally tempted towards this view, but I'm too lazy to elaborate right now).