Once you buy some coins, buy more than you need then become a reseller via localbitcoins. Reduce the pain for the next person!
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Love that site. Have gotten calls from it in the past.
If you're in (very) Northern California, I'll sell ya some bitcoins for cash, in person or by mail. I'll also sell for USPS money order, verified personal check, ACH, or possibly, commodities. I will also sell bitcoins for paypal to well-trusted buyers (no first-time customers for PP)
BitcoinsDirect sells for cash in the mail.
Aurumxchange has offered local bank cash deposits in the past, and made some recent announcements about trading bitcoins directly on their site as well.
on freenode #bitcoin-otc you can find many people who'll sell for cash, check, money order, LR, ACH, SEPA, wire transfer, and, really anything you can imagine
OP, you are quite correct that getting fiat money into the bitcoin-attached financial world isn't terribly easy. However, once you learn your way around the parts of the traditional finance world that you're unaccustomed to dealing with, it does become easier.