Best tool money you've spent

[Handplanesandmore]

The dumbest...bought from WN S&S the biggest, badest Porter Cable dove tail jig and a few bits.  IIRC paid $600 (came with a VCR instruction tape), before I ever tried it, I learned hand cut dove tails

You will never forget how to handcut dovetails (like riding a bike), but the dovetail jig is an animal to work with, if you don't use it often. You will constantly need to go back to the manual to do the settings, and worse, most jig manuals suck.

We should blame Norm Abram for our worst tool buy......
 

Simon

[Arlin Eastman]

First I would say the common everyday Pencil.  Then the tape measure and square after all of that it would have to be the bandsaw or Lathe.

[SawDat]

Mortise Pal.
Best $100 I ever spent.  I no longer dread making mortises.   Simple, elegant, well built and ... no longer available!

I treat it like glass as I depend on it, but can't replace it.

[Admiral]

You will never forget how to handcut dovetails (like riding a bike), but the dovetail jig is an animal to work with, if you don't use it often. You will constantly need to go back to the manual to do the settings, and worse, most jig manuals suck.

We should blame Norm Abram for our worst tool buy......
 

Simon

The thing about dovetail jigs is that they are useful when you have to do cabinet work, with 20 or more drawers; then it earns its worth.  For one off pieces, I'll do them by hand, but for semi-production work, the initial setup is worth the time. Clean, accurate and fast.

[kdouglaslee]

I assume you're talking about power tools, in that category I'd say the $100 that I spent on my Forrest table saw blade about 17 years ago has been well worth it, or actually it was worth it, I had to replace it last month.  I sent it in for sharpening for the umpteenth time, the factory called and said they would need to replace so many carbide tips that it would be cheaper to buy a new one.  So I did, only this time I got the one with a few more teeth than the Woodworker II.  So far so good, it leaves such a smooth finish I would only make it worse by sanding it.  

But the absolute best tool money I've ever spent is on my Stanley No. 8 "wireless" jointer, I use that sucker on just about every project.  I have fancier and more expensive hand planes, but my No. 8 is truly my go-to guy.  You can see it in my daily workbench pic that I posted earlier, here's a smaller version of my 

    No. 8 in the wild.

[kdouglaslee]

The thing about dovetail jigs is that they are useful when you have to do cabinet work, with 20 or more drawers; then it earns its worth.  For one off pieces, I'll do them by hand, but for semi-production work, the initial setup is worth the time. Clean, accurate and fast.

I hated my Porter Cable dovetail jig so much that I sold it on ebay after I finished a major kitchen remodel.  Once you get it set up correctly it's still a pain in the rear to use, but yeah, you can do a lot of drawers fairly quickly.  Hated setting it up, though.  On the bright side, I sold it on ebay for very close to what I paid for it, so there's that.

[JSpill]

Best tool money spent-- 1973 I bought a used Craftsman table saw manufactured by Emerson Electric for $125.00. I still use it and have used it to build cabinets, chairs, grandfather clocks, toys and tables. It still passes the "nickel test".

[Splinter Puller]

My best purchase was deciding to buy an Industrial Delta Oscillating Edge sander.   They retailed above 2k but I won a bid for one for below $500.   The sander is a game changer on many procedures in the shop.    Drawer does not fit perfect... just sand a bit of the side off...    A panel needs to be slightly resized... just sand it.  So quick and easy.   Even easing the edges of panels... just touch them to the sander and raise them up through 90 degrees for a fast, safe 1/16" roundover edge.

Love this tool.

[John Mihich]

I paid 450 for a Delta 18/36 drum sander,  I use it all the time.  I bought it from my brother who upgraded to a WIDE sander.  The other thing was a 1990's Table saw - $100 at a garage sale.  It's not the best in the world it has been great for me.  The rest of my tools I paid full price - all new; oops my radial arm saw was a good buy also - new/used 1980's Craftsman model for $60; guy bought it new but never used it.  I had to finish putting it together.

[®smpr_fi_mac®]

I dunno. Every stationary tool I have was either bought used at a really low price or, in the case of my table saw, given to me. They're all old; my table saw and band saw are the only tools younger than me, and they're both early 90's.

So, of them, the Shelix head I put in my PM100 planer. WELL worth the $850 I paid for it. I think I paid $200 or $300 for the planer.

Re: The edge sander above: They're spendy, which is why I'll start building one next month. For the reasons listed, I bet it'll become one of my favorite tools once it's done.