Its not only a matter of skill, I had a wallet a year and a half ago when I was first checking it out... Its a matter of what I want to spend my time on... even the online exchanges are a pain to deal with compared to just accepting a credit card. I have no desire to spend time keeping track of some file.
If bit-floor comes back online, I think the only answer is to just sell every bit-coin as soon as I get it. The issue with doing that is that it really ups the cost of accepting bit-coins, as there will be higher percentage of fees if im doing lots of little withdrawals.
What about the blockchain.info/wallet ? This system doesn't have access to your private keys, because it only decrypts them in your browser when you log in.
You can get it to send an encrypted backup to your email - so even if the blockchain.info servers were to just disappear, you'd still be able to recover your bitcoins.
With the capability to 'pair' your account to an app on the android phone, it really is quite convenient.
Surely this would suffice to hold a few hundred/thousand dollars at a time until ready to squirt them into an exchange?