Firstly, Jason, grind your own. Don't just get a pound, have the store grind it, and keep it in your freezer. The timing of grinding is crucial for a good cup of coffee or espresso.
For drip, you really don't need anything fancy. You can get just as good a cup of coffee from one of those plastic cones with a melita filter as you can from a $300 coffeemaker. Those things are just giving you conveniences like timers and larger quantities. If you want to get fancy with drip, I'd recommend trying courser grounds with a French press.
But for espresso, well, you get what you pay for. When I first went to Prague, I developed a taste for espresso. After I got back, I was pretty unhappy with most local espresso. So I decided to buy my own machine. After doing a bit of cursory research, I realized a snooty guy like me wasn't going to be happy getting some $50 machine at Bed Bath and Beyond.
That's when I met Sylvia. Since then, I've been a very happy espresso drinker. And I'm certain I've saved money in the long run because I simply can't abide a store-bought espresso from someplace like Starbucks where they use those dreadful automated machines. That stuff is utter swill.
Sylvia isn't like those $1000 restaurant machines that monitors the temperature, but she can still pull a perfect shot. I recently learned something called "temperature surfing" to find the sweet spot for when to pull the shot.