For your three questions:
1. Based on what you want, the Vetrano seems like a better match (since it can be put on a digital timer), and the intro price is a very good one if Chris still has machines available from his first batch. You should know that he also has a 30-day use-it-and-if-you-don't-like-it-return-it policy, so you get some protection even though it's a new machine that has no history (yet). Based on Chris' reputation and having talked about this machine with him at some length, I decided to order one sight unseen (I had previously been leaning towards a Bricc). If you want a Vetrano, you'd better call him right away, or you'll be waiting until February and paying more.
Alternatively, you can always wait for something newer and better, especially now that what was a gulf between $600 and $2000 machines is getting bridged, or perhaps an S1 might be to your liking (check out the gift specials in the Marketplace forum for some good deals), but I decided on the Vetrano instead of the S1 because the latter is not quite the machine I want for that price (the Vetrano takes up less counter space than the S1, by the way). Perhaps in a year or two the double-boiler machine that I really want at a sub-$2000 price point will appear on the market, but I don't want to wait that long when I can have a machine I'm pretty sure I'll be more than happy with in the meantime.
2. If the grinder you got as a gift is a ProLine, have a look at Mark Prince's short review at
http://www.coffeegeek.com/proreviews/firstlook/kitchenaidprolinegrinder. It looks like an OK device for $200, but if you can get a full refund for it, you might want to purchase a Macap ($375) or Mazzer ($420) instead, which are doubtless better (keep in mind that the first edition of a product is more prone to problems, and the KA is very new to the market) and worth the difference in cost (either one will probably outlive you). For a Vetrano/Bricc class machine, you'll profit from a VERY good grinder.
3. Practice makes perfect.
