Well years ago I over filled my old Craftsman double box and it would not roll anymore. So a couple years ago I was at Sam's Club and they had a large Stainless Steel double high box for ~$700 after taxes. It is a real nice box with ball bearing slides & non-slip pads for the drawer bottoms included. I think it is 40" wide and has real nice wheels.
Load your box with the heavy stuff in the bottom to prevent tipping!!
I keep my drills & bits in my old box. Hole saws would be in there as well but I seldom use them so they are on a shelf near my work bench. They belong with drill bits, since they work with a drill.
I moved most of my stuff into it and have it organized this way:
Upper box:
Top: Misc stuff, VOM, Sunglasses, paperwork, goggles, etc.
3 drawers across top
L) Punches & Chisles. (M) not sure, (R) Wire strippers, needle nose, dikes etc.
2nd drawer: files,
3: Glues, Loctite, RTV, Gasket maker, Teflon tape, small tubes of grease, etc.
4 : Screwdrivers: Phillips left/ Straights right.
5: Sockets (SAE), ratchets & Extentions, adapters, swivels, plug & oil sender sockets, plug gap gauge, etc.
Lower Box
1: Pliers, Adjustable wrenches, Vice grips Channel locks, tape measures, anything I need often and quickly.
2: SAE Wrenches
3 Metric Wrenches and Sockets
4 Pipe Wrenches
5 Hammers
6 Anvil, short piece of train track, Pry bars, BFH, etc. I put the 50# anvil in this drawer after I almost tipped the whole box over on myself!
My old box has Drills, body tools, tire repair, allen wrenches, saws. All in thier own drawers. It needs cleaned out & re-orginized.
Have fun!