I guess I'm somewhere in between you two.
I can be super OCD with game file/final file naming...
"PackGroup/Model Name_Mesh/UV ID_Texture Set ID_Shader ID"
Some people find my naming conventions confusing but they do the job I require of them.
But my local file directories are less specific (mostly because I pack stuff into .PSDs.)...
Meanwhile, my working file directories are a mess...
And my weapon work directories can be a mixed bag.
I try to keep a weapon's root directory relatively clean with the export-ready maxfiles, final PSD comps and scene maps...
(I have NO idea why I marked the world and VWEAP models with "PA"... Sometimes I have odd typos that get propagated as the hours wear on and my vision gets blurry... For all I know, it may have been an meaningful abbreviation at the time)
In my "Work" sub-directories, I keep my max files basically as a logbook. I can go back to whatever stage if I need to grab some random boolean object from an earlier stage or whatever. The more tightly packed the file versions are indicate how uncertain I am of something breaking or not...
And just to add some comfortable mess, I also have random reference pics, various texture bakes and UV guides, various skinning envelopes, raw PSDs, random orphan PSDs for shader compositing, layer merging, etc. stashed in there...
I generally know what/where everything is in the short term but if I return to a project after a long delay, I can need a bit to get reorientated.
Gigabyte P67A-UD4-B3, Intel Core i7 2600K (passmark 8555), 16GB Corsair DDR3, EVGA GTX 970 SC (passmark 8637), Win10 Pro 64-bit, Primary monitor @ 1920x1080, secondary monitor @ 1280x1024