My first kit, a present for Father's Day, was a one gallon kit. After brewing that, I brewed a beer with DME. And then I decided to experiment with grains. My parents have an old Peugeot mill (a heirloom from my father's grandfather).
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This crushes things, and was very nice for crushing grain, albeit a bit slow.
I did upgrade in the course of time, but not that much. I brew between 8 and 10 litres (24 to 30 bottles).
I also split up my brew day. One evening I do the mash and the filtering, and pasteurise the wort. Then I seal off my boil kettle so that it can cool. The next day I do the boil. After the boil I seal it again, and the yeast is pitched on the third evening.
I did buy a real malt mill, a pH meter, a cooling coil and an RO system. Those were the most expensive things. But for most part I try to use simple things. My filter system consists of two buckets that I got for free in the fries shop.
One of the things that convinced me that it was possible to brew small amounts was
this article.
I also wrote my own brewing model, so that I can brew starting from how much I want to brew, what the ABV should be, what the percentages of fermentables should be, the attenuation of the yeast (which I also keep, and use the statistical average of their usage). I only need to add solutions for the hops, to get the amount needed based upon boiling time and desired IBUs. Something for the winter months.