I personally have no problem with spending a bit of cash to get the right gear, but I have a feeling the other half will

Would you recommend getting the Jalapeno or sticking with a Pi and just expand with more USB's?
Well it depends if you see that bit of cash as extra money or essential to your mining. If you see the cash as essential then don't buy the jalapeño, because you won't be able to earn the money back in some time. Although the price of the bitcoin could potentially rise over 200 by the end of this year but nothing is guaranteed. The amount of bitcoins you can mine if you have a jalapeño in a new server should be around ~1.5BTC per block. Not counting in the the difficulty rises, the rise of the bitcoin price, and the pool fee you should get ~2.5 bitcoins a month. But keep in mind that this is only my opinion and we are ruling out the factors that can unbalance this equation. Also, you can try
http://p2pool.org/. Happy Hashing
