1. I'm not interested in running multiple computers at max cpu usage for weeks to try to generate a rather trivial value of coins, especially when I know GPU users have vastly higher efficiency
That's totally understandable, but I think you are missing the point. The point to Bitcoin is not to generate "free money" (as if there is such a thing). The point is to back the coins with something tangible -- electricity (aka "energy"). Also, this is about the only way you can carefully control the minting of the currency.
All of the world's currencies are backed by energy. Human or otherwise. Bitcoin is a little more direct. The generation (work/labour) creates hashes that are valuable (money) to other computers/people running the same program. Why is it worth something? For the same reasons that FRNs are worth something: people accept it for the trade of
real goods and services.
It also sounds like you feel inadequate because you can't generate as fast as others. Why not sell something? Selling real goods and services is far more profitable than generating. Plus, there is the added benefit of adding value to the currency itself. Generating isn't the "be-all" and "end-all" of Bitcoin.
I don't see the point in generating for gains. Some people advocate generating to help secure the network from attack -- sure I can see that point. I also see that as a public service, or a donation to the cause. Where I live the electricity costs are very cheap, but I'd still pay more in electricity than value that I'd get from the coins. I'll leave the generation to other people, and buy the coins from them for my exchange business.
2. The mechanics of keeping my wallet files private and constantly backed up with a fresh copy gives me "data stress"
Do you keep your life savings in your wallet in the real world? The solution to this is simple: diversify.
3. All software has bugs. Software that is related to money is an inevitable target of attacks, and there is no FDIC backing or legal system remedy available in the case of problems
Sure. Hopefully with enough eyes on the source code the major bugs can be ironed out. The Bitcoin software will never be perfect, but considering the alternatives I'd say it is pretty good.
The FDIC is bankrupt. Google it. Also, what good is the FDIC if you lose your wallet in the real world?
Legal system remedy? Get real. Have you ever actually tried to sue someone? The lawyers largely benefit from any legal conflicts. The best way to operate is based on reputation. It is what humans do naturally anyway.
4. I don't really know how to document and declare transactions in bitcoins for legal and tax purposes and I'm scared of getting it wrong
That's easy. You don't claim the Bitcoins themselves. You declare the dollar-equivalent value of the goods that you received in trade with Bitcoins.
Cheers!
The Madhatter