Okay, so every time I play FNV (and FO3 to a lesser extent) I run into inventory management problems - specifically, that I frequently end up overencumbered. This seems to happen whether I have a carry capacity of 170 or 250, and no matter what build I use. It's part of the reason I always always use two companions (one humanoid, one robot) even when it would have made more sense to go alone. It's also why Strong Back is a perk that I take in every single playthrough, even with the limited amount of perks available, and I've taken the Long Haul perk whenever possible. For RP reason I tend to keep a proper armor for combat (say, combat armor), 'wilderness' apparel and 'formal' apparel. I suppose this contributes to the problem, as does the fact that my ammo has weight because I play on 'hardcoe' mode.
I'd guess that it's also because of how I loot - I tend to take all weapons, armor and food items whenever I kill someone. This has always been how I played games with loots and inventories. I've always assumed that this was the way to play, but it recently struck me that I pretty much never read of people complaining about not having enough inventory. I personally find it quite disruptive to have to stop midway through killing some Fiends/Legionaries and have to fast travel to a vendor.
So how do you guys organise your inventory and decide what to loot and what to discard? Or do you just svck it up and frequently interrupt your dungeon-crawling to make vendor trips?