Howdy fellow Chicagoan. My first foray into home espresso was a Gaggia Classic and a Baratza Encore. That was more than enough to replace my forays into the coffee shops.

A friend of mine uses a cheap breville and preground coffee and is satisfied, so I think it all depends on how picky you are.

Uniterra Nomad. Workflow is a little fussy but it works great. I've found that especially on lighter roasts, using lower pressures helps a lot.

Doesn't really answer your question, but I've been really happy making "faux latte"s and such with my Moka pot. A little inconvenient to clean, but definitely takes up less space than a mini espresso machine.

Beans, grinder, technique. Then machine.

I’ve had a number of machines (decent now) and it isn’t required to make something really good. Learn the basic techniques to get the flow and pressure right with your unit of choice. Dual boiler or switched boiler (either steam or brew via a switch) is my suggestion there, as the heat exchangers are great, but you have to play with them to know how it works.

Learn Wdt.