Since I'm having fun spending YOUR money, I ran out to my shop to look over my tooling to help you spend some more!
Nice tool box to store your tooling (I use a HF 26" x 22" roller base and upper chest).
A lot of my projects involve using 5-C collet blocks. They're handy for knocking 2, 3, 4, 6 sides on a round.
Machinist clamps and kant-twist clamps
Mist coolant with mag base. I've had good luck with my <$20 import that is a siphon type. Drop the pick up in a milk jug of coolant, hook up the compressor and spray away.
Rags to clean up the aforementioned coolant
Machinery's Handbook
Quick reference drill/hole size guide. Mine is a file off the web that has sizes of numbered drills, letter, fractional and metric. Also frequently reference a page that has tap drill sizes for various class threads (highlighter run over the 75% common ones) and clearance holes (obvious on fractional sizes, not so much to me on numbered sizes).
Over-under reamer set - mine goes from 1/8" up to 1/2" by 1/32"'s. Sizes are over/under the target by 0.001". Handy for press in tight dowels or loose fit.
For edge finders, they are handy to have in 1/2" and 3/8" shanks. Saves a collet change in a lot of cases.
I use a wiggler with a point end for finding center punched holes.
Blake co-ax indicator. Used for quickly finding the center of a hole or boss. Mine also has a spring-loaded center for finder a center-punched hole.
Depth stop on the quill can be handy.
For more edge finding, I also have a Borite electronic (ferrous metals only), and a couple of SDA laser center/edge finders. I've got one with crosshairs and one with concentric circles. The circles one is nice for a quick find on a drilled hole. I'm usually accurate within 0.010" or better.
I've also got a centering scope though I can't recall ever using it. It has a microscope-like eyepiece and a cross hair to find a feature on a part.
Slitting saw arbor and slitting saws.
Corner-rounding end mills.
Vise jaw work stop
Miscellaneous cutters that are job-specific like tapered end mills, dovetail end mills, key cutters, etc.
End mill holders with set screws. I tend to be pretty conservative on my cuts and haven't experienced tool pull-out with end mills in collets. These holders have a better mechanical lock than collets.
1-2-3 blocks.
T-slot cleaning tool
Magnetic pick-up tool
V-blocks
Micrometers, dial calipers, depth mics, angle blocks, machinist squares.
Toe clamps for work holding
More of a luxury than anything, but I also have a Quillmaster with the QLR head. Also, a right angle attachment.
Angle plates
I've got photos of my mess(organization) if you'd like. They'd give you an idea of how to store 200 gallons of crap in a 5-gallon bucket.
Bruce