I agree with you, for newbies Steemit funding is quite confusing and not intuitive. I like your idea of a trusted third party for small amounts to get people started. Maybe even something you could top up with a debit card?
The main entry point to Crypto seems to be bitcoin. In one sense there are so many exchanges and ways to get fiat into the ecosystem its easy, but it is scary for a newbie; "wallets", "exchanges", "fiat" the jargon is endless!
Even for advanced crypto geeks I think the Steemit wallet and 3 types of steem are confusing. I think some more thought should be put into the wallet interface also.
Thanks for your thoughts. I'm going to be working on fleshing out this plan over my next few posts. We might need a tame 'whale' to help by acting as escrow; someone who's happy to take the paypal donation, send the steem and then forward the paypal credit to a central Steem pool in exchange for more Steem.