I bought an Iwata HP-BC2 in 1986. It's still my main brush. Still original needle and nozzle. 30 years of flawless service.
In the past few years I bought another two Iwatas, both gravity feeds, one for quick color changes on figures, one for large areas and priming (Don't remember the model numbers off my head). The only thing that changed over the 30 years: the box is plastic instead of wood.
A bit of info on Iwata, they are similar to Tamiya in terms of offering two different packages for overseas vs the home islands. My latest Iwata is going for $500 in the States, which includes a beautiful metal case, hand grip moisture trap and a hose. I bought the same brush from Japan with no accessories and a cardboard case for $160 shipped.
Compressors are where you can skimp. All you need is a device that delivers air. It could be an old tire (tyre) for that matter. The only differences will be how loud it is, how long it lasts and whether it cycles constantly or stores air. Depending on your needs. If you are going to spray in a shop at night above bedrooms, you need to go quiet. If you are going to work in a shed outside and have use for a big comp that can run other tools or work on the car, go big.
A good brush, a good regulator and moisture trap and you'll be happy. Consistency is key.
In terms of a crappy brush, you can also fill your mouth with paint and spit it through a straw. Eventually you'll get good at it. Eventually. With enough practice, you'll learn how to control the pressure like a saxophone player, you'll learn where the paint wants to build on the straw, you'll figure out the best aiming point and paint thickness. Just like a cheap brush.
