Bball!
Man, one slippery slope hobby ain't enough for ya?!
Seriously man, good coffee can get very expensive very quickly. However, if you're smart, you can actually save some money in the long run.
To answer your question, however, (and I know you will not want to hear this, because neither did I) the MOST important purchase you will ever make in this hobby is your grinder. Especially if you are thinking about espresso. Yes, the longer you press the button, the finer the grind is... But I'm assuming that at $20, you have a standard kitchen grinder and not a burr grinder, which is what is required. And a blade grinder will not grind for espresso.
Buying a great coffee machine after a terrible grind is just not worth it. YOu will not get what you paid for in the machine.
My advice: Buy the grinder first, and then the machine. There are good recommendations from all over the net, but off the top of my head: The Baratza Vario (as low as $300), and the Rancilio Rocky (~$400). But there are certainly cheaper ones starting at 150-200 also which apparently are outstanding.
I would strongly advise against an all-in-one super automatic machine (like the DeLonghi above). Many technical reasons for that, (which I don't know if I believe or not) but at the end of the day, my Saeco Odea just didn't cut it in terms of flavor and crema.
If you do want to buy a machine first, then +1 on the Silvia. Had used one for a long time, and my new Silvia / Rocky combo is on its way and should be here later this week.
Whatever you decide, good luck to you. Nothing like a sweet, thick shot of espresso in the morning! Meantime, some low-budget coffee pr0n for ya! [ame="http://www.youtube.com/watch?v=zk1kzRkCe_o&feature=related"]Naked Portafilter shot with Rancilio Silvia - YouTube[/ame]
Enjoy!