I always try to mix it up. I have almost 100 knives, SAKs, and multitools, and I try to give almost all of them some pocket time.
Some days I keep it simple and just bring a knife. Some days it is a knife or two and a SAK. Maybe just a SAK. Or 3 knives and a multitool. Maybe a clipped folder, a SAK, a slipjoint, a multitool and a neck knife. It just depends on where I am going, what I am wearing, and what I plan on doing.
At work I will tend to bring good work folders, or fixed blades. Examples are Strider SMF, Spyderco Military, Benchmade AFCK, Victorinox Super Tinker, Buck Short Nighthawk, Ka-Bar Warthog, Leatherman Charge Ti. These knives/tools are pure users. I don't mind scuffing them up on a pallet and I squeeze by, and I don't mind them getting dirty and inky. I also wear jeans and a belt to work, so weight and size isn't much of an issue. I can carry a Skirmish in my pocket no problem, with a Leatherman on my belt and a SAK riding at the bottom of the pocket below the Skirmish. At work I can also carry a fixed blade without sending people running.
But when I am just out and about I often wear shorts. This makes a fixed blade less practical (no belt), and I would probably attract a lot of attention with a fixed blade if I was wearing jeans that day. In shorts weight and size are an issue. And in public, sheeple-friendly is a good thing. So a Manix is now too big, heavy, and scary. A Buck Mayo TNT or William Henry Titan is now my choice. Outside of work I don't have to worry about ink and dirt, or scuffing on a pallet. So my more "fancy" knives get used when I am just out and about. They tend to be better for the sheeple, too.
Sometimes I am in the mood to carry something expensive. Sometimes I want a high-end knife in my pocket and even something "cheap" like a Skirmish, 710, or Manix will not do.
Sometimes I am not in such an elitist mood and a SERE or Skirmish is what I want.
Sometimes I am really not in a knifey mood but want or need a knife (I *NEED* a knife for work), so I will carry something inexpensive like a Native or Leek to "save" my more expensive knives from getting worn and dirty.
I will sometimes bring a flea market junker as a knife to lend out, or to use for very messy tasks that I don't want to put my good knives through. This is only sometimes, though. Usually I would rather hand someone a good knife and have them think "Man, Brandon is really into high-end knives" rather than "Why did "the knife guy" at work just hand me junk?". I also consider all knives as users, so I often like putting my expensives knives to task at dirty or hard jobs that most people would use a beater for. But sometimes, when I am not in such a knifey mood, I would not get as much joy from using one of my better knives, so I might as well use a junker and just get the job done.
A lot of it has to do with picking what is appropriate for the day ahead. A "load out" for one day might be inappropriate for another day. That is why I like such a variety of knives. Dress folders, large beefy folders, small beefy folders, small fixed blades, large fixed blades etc.... Sometimes I want just a William Henry Titan in a slip/clip case clipped to my shorts (or slacks). Some days I want a Strider SMF, Leatherman Charge Ti, Victorinox Super Tinker, Becker Necker, and Ka-Bar Warthog. Though, that is probably excessive
And sometimes it is just a matter of mood. Sometimes I am feeling "tactical" and prefer the performance and ruggedness of an SMF to some namby-pamby all-for-looks dress folder. Sometimes I am feeling very classy and prefer a sleek, stylish Mnandi to some cheesy, immature ninja knife.
I like variety!