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Any advice on upgrades from where I'm at now? I want to eventually get a better machine, but for now, I think I really want to get a better grinder. I've really been considering a Rancillio Silvia with a Rocky grinder, but I think I may want a better machine than that.
Advice?
Sounds like you've got a good entry set up. It's very close to what I started with, and that served me well for the time I had it.
First and foremost, are you using fresh beans? Within two weeks of roast date (not 'Best By' date)? If not, that's going to be the easiest way to improve your espresso. After that, you might consider equipment upgrades.
A better grinder really is good investment for espresso. I would strongly recommend looking into a used commercial grinder if you have the space for it. They can be had for a great value, but of course you have to be somewhat careful if buying from Craigslist or Ebay (My latest came from a CL posting, and it worked out just fine). A stepless (meaning infinitely adjustable) grinder is very nice for dialing in the perfect grind, but it's not absolutely necessary - most commercial grinders, I think, have sufficiently small step sizes if not stepless. Still, go for stepless if you can. I've used both - it's worth it. A Mazzer Super Jolly is a popular choice as they are relatively easy to find used.
I'm not sure what the rules are about promoting other forums, here, so I'll just say that there are some coffee specific forums where you can generally find well-cared-for equipment.
If you don't have the room or desire for a commercial-sized grinder, I've read lots of good things about the newish Baratza Vario. However, it's pretty new, so a used one will be hard to find, and a new one will be more expensive than a good deal on a used comm. one. Maybe do some reading on that.
As for the espresso machine:
I owned a PID'd Silvia for about a year, and it is a very capable machine - a little touchy about grind, but capable of great espresso. For the retail price of a new one, with a PID, though, you can spend a little more and get lots more machine (or again something used). The main thing to consider about the silvia is that it's still a single boiler dual use (SBDU) machine, so you have the wait times between pulling a shot of espresso and steaming milk. If you only make one drink at a time (or primarily drink straight espresso), this is probably not too much of an issue. Multiple drinks can become a pain though, so consider that.
I recommend doing some reading on a coffee forum. As you can imagine there are tons of posts that will help answer your upgrade questions.
