Your inquiry isn't stupid at all OP. I'm in pretty much the same tool use and storage situation you are in. I never know what I will be working on next and I have tools for pretty much any job. I also hate spending money on tool storage. I would rather put that money into tools, so my tool storage is very similar to yours and I'm very happy with how well my small shop functions. I have multiple smaller garage sale tool chests, used gorilla type racking accumulated from CL for larger items, lots of milk crates/square plastic buckets, and garage sale file cabinets for much of my bulk tool storage.
What I do-
I have a small lightweight carry tote that's the first thing I grab for any job. It contains all the common hand tools that most jobs will require the use of. Things like a tape measure, wire strippers, water pump pliers, needle nose pliers, adjustable wrench, utility knife, snap blade knife, a couple picks and/or toothbrushes for cleaning, very common screwdriver types and sizes, pens, pencils, electrical tape, etc. Beyond that I have a rather large heavy duty oven roasting pan with two handles that I use to carry around most of the supplemental tools I might need for a specific job. That roasting pan will sit on the ground outside if I'm working on something underground like a sprinkler system, or it will often sit on a repurposed wood framed tv tray next to me if I'm working in a seated or standing position.
Larger metal tool chests/drawers are almost exclusively used for tool categories that consist of lots of items. Things like wrench sets, socket sets, insert bits, pliers, etc. All of that stuff is packed tight but highly organized because I want to be able to access it quickly and visually notice if something is out of place or missing. Smaller metal tool chest drawers are used to hold task specific tools. I have one small drawer for all my spark plug tools and sockets, one for all my tire related tools, one holds my manual impact drivers and all my impact bits, one holds all my pipe/tubing cutting and reaming tools, etc.
I use my file cabinets mainly for lesser used tool categories or specialty tool categories. For instance, in one of my file cabinets one drawer has all of the various shop funnels I use, one drawer has all my painting supplies and brushes, one drawer has all my drywall tools and supplies, one drawer contains all my masonry hand tools, and one drawer has all my layout tools (chalk lines, tape measures, plumb bobs, measuring reels, string lines, laser levels, etc). The items in each drawer are either piled up loosely or lightly divided and organized within each drawer. I find it too much work to formally organize tools that are irregularly shaped and also aren't used constantly, but I don't like searching for tools either so minimal organization in each drawer is often needed.
I slowly accumulated used Gorilla style racking for larger tools and/or bulk tool storage. I store things like circular saws, sawzalls, pipe threading tools, chainsaws, jack stands, etc. directly on the racks. The bottom shelf is often placed high enough off the ground so that I can roll things like my floor jacks almost all the way under the bottom shelf when they are not being used. I also have a bunch of plastic milk crates or square plastic buckets that I use to store supplemental items next to the tools on the shelving. One milk crate holds all my circular saw blades and chop saw blades vertically with cardboard separators between each blade, one milk crate holds all my 4-1/2" and 7" angle grinder wheels, one holds all my replacement bench grinder wheels and wire wheels, one holds all my chainsaw accessories (chainsaw chaps, mesh front hard hat, hearing protection, spare cutting chains, chainsaw specific maintenance tools, etc.). I also have a square plastic bucket that holds all my smaller yard and garden tools like trowels, pruners, hose end sprayers, soil knives, yard work gloves, etc. I grab what I need for a small job or take the whole bucket to where I will be working outside if I will be doing more varied yard work.
Flexibility is key in how I organize everything, and buckets or milk crates are great for any tool category that's convenient to have in a very portable form. Mentally, I think of each storage drawer or vessel as being it's own sort of ecosystem. That one vessel can be fine tuned and organized as much or as little as needed to make the tools easy to access and work enjoyable.
Good luck OP.
