I've only brewed 3 batches and have been AG on all of them. I was lucky enough to have a friend in the hobby that has been a great resource for me every step of the way. Let me give you my line of thinking.
I decided that I would want the ability to do 10 gallon batches eventually so what would be the point of buying a smaller kettle now only to have to buy a bigger one down the road and lose my arse on the first one. So I bought this dude
here for less than $70 before shipping. This is a good quality kettle with plenty of wall thickness. I installed the ball valve and thermometer/sight glass combo myself which was very easy.
I picked up a banjo burner made by bayou classic for less than $90 which will allow me to do whatever size batches I see fit.
I was lucky enough to get a very large igloo marine cooler from my parents for free and modify it into a mash tun by picking up a cheap ball valve, brass nipple and a few other inexpensive fittings at home depot. Probably spent about $30 on this.
I bought a 'brand used' thermenator plate chiller from the classified section here for $80 which has really been the way to go in my eyes over an immersion style chiller.
At this point I strictly ferment in half barrel sanke kegs. I have 2 that I bought for $25 and $45.
I also bought 5 corny kegs for $30 each however I had to recondition them with with new o-rings which were not expensive. My reason for going with kegging over bottling was because I was given a freeze that I intend to convert to a keezer eventually. Freezer can be found for cheap on craigslist and can be used as a kegerator with a CO2 tank, gas line, beer line and post fittings and picnic tap without having to go all out and finishing out the keezer like you see on this site. Mine is very simple at this point and I will finish it out later as time and money allow............ Bottling may be a better option for you. Probably would be a bit cheaper depending on the deals you can find. Bottles are generally cheap and or free a lot of times. I've never bottled before but it seems pretty straight forward (all be it time consuming) to me.
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It took me some time to collect all of this. Believe me, I was extremely anxious to brew my first batch but I took my time and got all of the things I needed to brew at the level I knew I would want to be at in a few years. There was a little more initial cost up front but in the long run you are going to save money. A lot of money!
The last thing I will say is that you can buy the fanciest stainless brew kettle there is out there. You can build the coolest brew sculpture the world has seen. You can buy the top of the line stainless conical fermenters on the market...................... Fact of the matter is if you adhere to the recipe's you see on this site, hit your temps, ferment in a environment that is temperature appropriate for the yeast you are using and take all necessary steps to ensure no contaminents are introduced during your brew process then you are going to brew some darn good beer that will rival what the other guys are making with all of that top of the line equipment. So find what you like, buy what you can afford and get to brewing. The magic isn't in the equipment, it's in the knowledge of your ingredients and the brew process itself. We are fortunate enough to have plenty of that knowledge at our finger tips here within this community.
Best of luck and if there's anything I can do to help just let me know.