You may want to unlaod those iPads sometime soon. As soon as Apple announces the next generation they are going to go down significantly in value.

I think he means a portfolio of investments in companies involved in the manufacturing and production of iPads, i.e. http://en.wikipedia.org/wiki/Ipad#Manufacture

It sounds like it would be a good idea, but you'd actually have to take a look at each of the companies, and figure out exactly how much each contract with Apple is going to bring in relative to their current revenue streams.

I think that he may also just be joking that an 'iPad-based portfolio' is not exactly 'conservative.' (I mean it's a brand-new product, it's still risky no matter how hot it looks to be in the market)

I hoping that was a reference to this classic Zoidbergism: http://www.youtube.com/watch?v=e3QRTToTLzI