As you said, your alternative a) leads to the same problem with viruses then the autostart-script if the finish solution does not ask you for your wallet password and ensure exclusive access to the keyboard during that time, which no Bitcoin Client does at the moment i think. Otherwise features like clipboard copy and paste would be deactivated in the Wallet's password dialog because it is an often used way to steal the input.

Alternative b) ends in an independent system, which only reminds you to pay something, and there are tons of Bill Managers & Reminder out in web if you just need something that helps you to send your payment out regulary. You could use one for USD and keep in mind that you mean BTC.

Here is another list with richest addresses from Jan 2013: https://en.bitcoin.it/wiki/Bitcoin_Ladder#Top_addresses
 

Try to make the QR-Code larger by zooming in to fill your screen.
Also try other QR-Apps. Sometimes zooming function on the mobile cant be used. I never had problems with zxing.
I only use normal Bitcoin Wallet on mobile with max. of 0.5BTC right now: It is enough for most cases and the problem is something else when they get stolen!

Satoshi will already be on the 0.00000001 BTC Coin 

https://en.bitcoin.it/wiki/FAQ#What_do_I_call_the_various_denominations_of_bitcoin.3F

I read somewhere, that payment-requests might be possible with bitcoin in a future.

Idea behind Bitcoin is that nobody else except you can take your BTC, so it should be obvious that you have to get active to send some BTC out
Perhaps an Onlinewallet supports recurring payments once it got credited with some Bitcoins!

In the meantime just use the API of bitcoin-qt with Autostart:
1.) Always start bitcoin-qt.exe with Parameter "-server -rpcuser=user -rpcpassword=password -rpcallowip=127.0.0.1 -rpcport=1234".

2.) Create timed schedule for execution (e.g. Schedule Planner in Windows every 1st of month):
bitcoin-qt.exe -rpcconnect=127.0.0.1 -rpcuser=user -rpcpassword=password -rpcport=1234 sendtoaddress 1dice6YgEVBf88erBFra9BHf6ZMoyvG88 1.0 monthly-satoshi-dice-payment
For more commands, see https://en.bitcoin.it/wiki/Original_Bitcoin_client/API_calls_list

And you have your standing order :-)

Attention: You open a door to viruses who already infected your computer to get easier to your BTC! It does not matter which username or password you choose. It will be always visible in process list. So be sure you do not use a wallet with many BTC, or you have a save (TM) computer

It is just another clone and fun currency: Enjoy life as a pirate, yarrr!