Short of a manual grinder + stove top setup, I don't think you'll find something that will produce a quality espresso and last at that price point.
A solid burr grinder (Baratza Virtuoso) will run you $200-$250 new (I bought mine used on eBay for about $125) -- these are pieces of equipment that last and are repairable, unlike most things these days. Control over the grind size and consistency are huge factors in espresso quality...definitely not a place to cut corners. I've also used Hario manual grinders when I'm on the road, though my experience is only with French Press/Pour Over with these -- should work fine, but you'll be cranking for a while to grind up the fine coffee required for espresso.
Rancilio Silvia is a well-regarded, no frills espresso machine that comes in around $700. This paired with the Virtuoso grinder produces a top-notch espresso / latte / cappuccino (comparable to what I've had at your niche premium coffee joints). Of course it takes time and practice to get everything dialed in just right. And just as the grinder quality is huge, so is the quality of coffee you're using.
I reckon the payoff for a $1,000 investment is about 1 year, assuming you replace 5 espresso beverages per week per year at $4 a pop. After that, a quality cup is costing you pennies on the dollar (coffee and milk).https://www.seattlecoffeegear.com
has a number of youtube videos that provide a lot of education and product reviews.