I would like to be doing relatively large batches and consuming my own beer only in five years.
Okay so you need to buy the equipment capable of brewing 10 gallon batches. There is no point in buying a five or seven gallon pot now only to turn around and need to buy a 15 gallon one in a year. Start off with a keggle or a 15 gallon pot for brewing (if you are going to buy a pot). You could spend some cash here. I got lucky on a unserviceable keg with a crushed upper lip. I also build my own false bottoms (I can send you the plan) using copper and a stainless steel colander. This also means a propane/turkey cooker style burner which you can find at yard sales or on craigslist for cheap. The only other items relevant to the size of a batch you intend to brew will be your mash tun (don't go less than a 10 gallon igloo (which is still small for some 10 gallon batches)) and the bottles or kegs to store it. So if you decide to build a mash tun as you move to all grain, buy a full sized one. There is no rush on the bottles or kegs though. As you grow in size, you can add those later.
I would deffinately be moving to all grain if not starting that way.
You will need to add a mash tun which will cost you the price of an old cooler and building/buying a false bottom or manifold. ($40ish if you score an old cooler and buy the copper for a manifold). There aren't many other special or unique items that you wouldn't already have from doing extract or partial mashes.
I live in the Raleigh/Durham NC area.
temperature control will be a concern when brewing from March to October. There are several methods (swamp coolers, water bath, ice bottles, etc...) I would just keep you eye on craigslist for an old fridge for cheap, then spend $60 on a temp controller and you are able to brew year round without concern over our lovely southern summers.
Right now not a lot of money, to start around 500 bucks.
You could go the barebones kit route then add a kettle, mash tun and a few other items or you could piece it together. Here is a quick swag item/price list assuming you are not going to do a secondary (if you are add $30 for a five gallon carboy).
6 gallon carboy $40 OR 7 gallon fermenting bucket $20
Airlock x 2 $4
5 gallon food grade bucket from Walmart bakery section to use as a bottling bucket $1
5 gallon food grade bucket from Walmart to use for sanitizing and stuff $1
plastic faucet for bottling bucket $4
bottling wand $4
10' of hose $5
bottles free if you ask around
bottle caps per batch $2
capper $20
8 oz of starsan $8
hydrometer and cylinder $20
thermometer (starter) $15
working fridge or freezer $50
Johnson A419 temp controller $70
Propane burner (CL) $30
This puts you at around $280 leaving $200+ for a kettle and mash tun plus other miscellaneous stuff I left out.
Room for brewing and storage is a two car garage.
This works.
This is surely something I am going to pursue.
Then what you buy initially, should be at the upper end since you will use it forever (i.e. GOOD thermometer, kettle, tun, and the like). Ask others how important something is or if you can go cheap. Better to spend now than to go cheap now and have to turn around and spend more later...says the guy who has purchased 6 x $15 thermometers instead of buying 1 x $80 thermapen.
Not sure about a homebrew club. Found some homebrew suppliers around the area and plan to speak with them in person this weekend.
I would attend a meeting and see about linking up and helping some of the member brew. This will expose you to guys at the various levels of brewing and help you identify what equipment or setup you may want to have. Plus you can obverse their processes which will help you develop your own. Ask the stupid questions and take notes. Other brewers can also be a great way to pick up items to build your brewing setup since we tend to upgrade some portion of our operation a regular basis. Brewing is a hobby that is SO cheap to do. Yet we end up constantly spending money trying to go bigger and better.
Keep the questions coming.