I've tried several times over the past couple years to get into HCE mapping, with varying degrees of success. Since my last attempt, I've lost basically all of that knowledge. Then it occurred to me to try a different approach.

With all tools and knowledge currently available to the community, where should I begin? Is there a specific tutorial that would serve as a better starting point as the others? In addition, what is the ideal toolset currently available(HEK version, etc.)?

Tools I currently have: 3ds MAX 2009, original HEK, photoshop CS5

I would always recommend haloguru"s making a map tutorial.
http://videos.halomaps.org/index.cfm?v=104
http://videos.halomaps.org/index.cfm?v=105

Who wants to make box maps? Watch fire dragons tutorial's he make's some very hard stuff simple. learn the basics of 3ds max.

I learned from halogurus tutorial and it gives you a very good idea of how to make a basic map.
3ds max skills can be learned anytime.

That tutorial starts at the start and ends at the end. Perfect.

Hmmm... Something just hit me, (in teh face), I have started getting into game making with unity, cryengine, unreal engine and another one I forgot (yes I experiment with all). But anyways, when you make a level in thar, you make a plane, bend it and extrude it and make it look like an elephant, then add ANOTHER box that is inside out, and that becomes the sky.

So in haloness terms, a box make is a map that does NOT have that concept. (And just an inverted box).

I just felt like sharing my thoughts... Don't judge me.