+1 to what Tex said.
Having had 15 espresso machines in the past few years, both prosumer and commercial grade, I can agree that the more tunable the machine is the better your end product.New Rancilio Silvias and Gaggia Classics hold their value much better than any new prosumer espresso machine. I commonly buy prosumer Isomacs and ECMs for $500 or less, and those machines retail for $1,500 and above. Not to mention the Silvia and Gaggia will be much easier to work on in the event anything goes wrong. Having rebuilt and refurbished all levels of espresso machines, I can definitely say that the more expensive the machine the more complicated / cluttered the inside is under the cover.
If the total budget for espresso machine and grinder is $2,000, assuming both items will be purchased new, I would spend at least $500 on a grinder. You can have a Speedster or GS/3 Marzocco, but if you have a cheap grinder you will have nasty espresso. On the other hand, if you have a top notch grinder and a PID'd espresso machine, Silvia or Gaggia on up to an Alex Duetto, Duetto II, Vibiemme Super DB, etc, you will produce much better espresso. The quality of your end product is heavily dependent on the quality / consistency of your grinder.
With that said, if the total amount available to spend is $2,000 and he would like to purchase everything new, I would recommend a Mazzer Mini, Macap MC4, Cimbali JR., or Compak K3 Elite. These range from $500-$700 dollars. I currently have a Cimbali Junior and a Mazzer Major, and use to have a Mazzer Mini, so I can attest to the quality of both of the brands and the quality / consistent grind they provide. Others within this forum have had great experiences with other grinders too. If you do your homework and contact some of the grinder manufacturers directly, they often have grinders they used in demos that they will sell you for a considerable discount. Another great option is to look for any of the above makes and models used on craigslist, then replace the burrs and you will be golden.
This would leave $1,300-$1500 for an espresso machine. In that price range I would go with a Moded Gaggia Classic. This is because of the machines overall simplicity and the ease with which one can modify the machine. Not to mention the great resale value of a PID modified Gaggia Classic if you ever do feel like upgrading.
If you can stretch your budget to $2,500-$2,700, and really need to have counter candy, get an espresso machine with both a rotary pump and a PID, as well as one of the above mentioned grinders. After opurchasing the grinder, that would leave you with an Alex Duetto II ($2,299), Expobar Brewtus III-R ($1,999) and Vibiemme DB ($2,299 available on some sites w/ a rotary pump).
I have had some very expensive and very large espresso machines, and when push comes to shove my personal favorite, for my palate, was my Elektra MCaL. I would recommend a lever espresso machine to anyone who really wants to dive into the experience. They can produce a far superior end product, IMHO, but do have a much steeper learning curve.
You do not need a prosumer or commercial espresso machine to get great espresso. In my experience they just take up more counter space, break more often and cost more money to fix. This is coming from someone who has been restoring and refurbishing espresso machines for 5 years, so I do take pristine care of my machines.
In response to the upgraditis comment, the only way to avoid upgraditis is to just buy a Speedster, La Marzocco GS/3 or La Marzocco Linea straight away. Then you just know you have the best, so you really can not lust for anything.
Just my 2 cents.
