I'd stick to Weber products for charcoal grilling. They'll last you over the long haul and aren't that difficult to clean up. Just get to it once ash has cooled (the next day) or get to it before the ash gets wet. Find a metal bucket to dump your ashes into and you'll be fine.
The One Touch Gold series of Weber BBQs have a removable ash pan which makes things easier. I'd also recommend a Weber chimney starter which avoids the use of lighter fluid.
I'd go with a lump charcoal or a natural hardwood briquette with a starch binder. I'd recommend Basques or Maple Leaf lump, Maple Leaf hardwood briquettes or Duraflame hardwood briquettes. The charcoal you use is a personal preference and I find that Kingsford and Royal Oak briquettes give a foul odour when first igniting. I have used Royal Oak lump in a pinch with fine results.
Deciding what other accessories you need is up to you!