If you're looking to drink on the cheap then this probably isn't the hobby for you, unless you're really stingy with your beer, make very few errors that force you to dump any batches, and are extremely patient to get all your equipment second-hand and on the cheap).
However, if you're still willing to get in, then this is my advice:
Buy each thing you need once and only once. In other words, buy the right type and size of equipment that you will still suit you 5-10+ years down the road. That's really hard to do though, because starting out you'll have little clear idea how far this hobby will take you.
I went with a 15 gallons SS kettle, a Blichmann burner, built my own 10 gallon mash tun, built a 50' 1/2" wort chiller, and over the past couple of years have bought various gizmos and contraptions, some of which I use all the time, others that I don't at all. If I could go back with the knowledge I have now, I'd probably save 1/4 of my cost or more. I *wish* I had have gone with a 20-25 gallon kettle in order to comfortably brew 10 gallon batches.
So, to figure out what you will likely be happy with down the road, I'd do this:
1) Figure out how big you want your batches to ultimately be:
a) Go into the 1-gallon brewers forum and ask them why they brew 1 gallon batches, how much beer it gives them,
how much they drink, how much time it takes them, and if they're happy at that size and with those methods.
b) Ask people who brew 5 gallon batches with top-up water the same questions.
c) Ask people that brew 5 gallon full batches the same questions.
d) Ask people that brew 10+ gallon batches the same questions.
Compare all the answers and decide what's right for you, trying to envisage down the road. For me, I brew 5 gallon, full boil, all-grain batches in a 15 gallon kettle. Ideally, I wish I had bought a 20-25 gallon kettle to comfortably brew 10-gallon batches. That would have saved me $200+.
2) Talk to people about stove top vs out-door brewing with a propane burner and compare their level of happiness with what they are doing and why they are doing with what they'd 'ideally' like to have or be doing. I brew outside with a Blichmann burner. I'm over the moon about that choice, but it wasn't cheap. Had I gone cheaper I probably would have eventually 'upgraded', costing me money.
3) Talk to people about temperature control. How do they do it and are they happy? I live in Toronto and I have a basement. This allows me to ferment in there about 9 months of the year without any additional gizmos (ferm chamber or swamp cooler).
4) Talk to people about chilling their wort. How much wort are they chilling, what's their method and are they happy? As I stated above, I made my own 50', 1/2" OD wort chiller and I'm perfectly happy (although it's an ugly S.O.B.). I saved money making my own, but could have bought a ready-made smaller one for cheaper.
5) Talk to people about crushing grains, mash-tuns vs BIAB, etc. Mills are yet another thing that aren't cheap, nor are they necessary if you're brewing extract or your LHBS can do it for you
but if you go all-grain and want to buy grains in bulk you probably don't want your grains stored crushed for overly long periods of time.
6) A whole bunch of other questions for each step of the way
bottling vs kegging, stir plates vs re-hydrating dry yeast, etc.
Short of hooking up with a local brew club and seeing various different peoples' processes and equipment in action (which would be super-ideal), you're doing the right thing by coming on here and asking tons of questions about equipment before jumping in. You'll save yourself money and more likely get a set-up that suits your purposes really well. Don't worry about sounding stupid or being bothersome. I'm on a few different internet forums and this is by far the friendliest of them all.
