Hello Bitcointalkers,

I live in a small university town that is crazy about coffee.

In a nutshell:
I would like to approach some coffee shops about buying credit with them.
Initially about 10 coffee shops $500 each. Alternatively fewer shops (depending on how many are interested) with larger amounts of credit.
The plan is to do a pilot study with about $5000. ($5k/6m seems reasonable.)
They then put a "Bitcoin Accepted Here" sign in the window.
People can then buy coffee on my credit with them and send bitcoin to my wallet at the point of sale.

The result:
Customers who want to spend their bitcoin can buy coffee.
I get bitcoin.
The coffeeshop gets money up front and carries no conversion risk.

Worst case scenarios:
1. no one wants to buy coffee with bitcoin and I need to drink $5000 worth of coffee.
2. people end up sending money to the wrong wallet/scam, they get free coffee, I lose money
3. bitcoin fails and I weep silently
4. I go to jail as a money launderer

I would like any feedback, ideas, etc. especially regarding how to avoid scenario 2.

Specifically: if there is anyone out there who owns a restaurant/coffeeshop/other merchant, how would you feel if someone approaches you with an idea like this?
Does anyone have a suggestion on how to handle the Point-of-Sale side of things?
Any lawyers who can give some pointers on what to expect with legal requirements when setting something like this up?
(I am hoping that keeping it small, i.e. 10 customers and sub $10 000, I won't have too many hassles or have to worry that I am technically a money transmitting service or something like that.)

My reasons for wanting to do this is firstly to do a small part in building the foundation of bitcoin economy and secondly to turn $ into bitcoin without using an exchange.

(Also:If this is not the right section to post this, please redirect me.)