Buy the cheap drill. Never buy the cheap jack stands.
A working line between the tools where price buys you nothing and the ones where it buys you a finished job and ten fingers.

Take the tape measure out of your kitchen drawer and hook it on the edge of a table. Pull out twelve inches. Now push the tape back in until the hook sits flat against the table edge and read twelve inches again. On a good tape, those two readings match, because the hook is riveted with about a sixteenth of an inch of deliberate slop to account for its own thickness. On a bad one, the rivet holes have worn oval and the hook wobbles, and your two readings differ by a couple of millimeters.
Two millimeters sounds like nothing. Cut eight cabinet parts off that tape and you've got a carcass that won't square up, and you will spend an hour with shims and bad language figuring out why.
That's the whole argument in one object. Some tools fail loudly and you know immediately. Others fail quietly and hand you the bill three steps later.
The test that sorts the two piles
Ask what happens when the cheap version underperforms.
If the answer is "it's slow and irritating," buy cheap. You'll survive slow. If the answer is "it lies to me" or "it lets go," don't. Measuring tools lie. Anything holding load lets go.
Everything else is negotiable and depends more on how often you'll touch it than on what it costs.
Never cheap: anything holding weight or storing energy
Jack stands, ratchet straps, lifting slings, chain, shackles, ladders, engine hoists. The failure mode isn't a wasted afternoon.
Buy stands rated well above what you'll put on them, and look for a stamped rating and a pin or ratchet mechanism you can see and feel engage. Cheap stands fail at the welds and at the cast pawl, and the ones that scare me most are the ones that feel fine for a year. Never get under a vehicle held up by a jack alone, no matter whose jack it is.
Ratchet straps are the sneaky one, because the strap isn't usually the problem. The hook is, and so is the ratchet's cam. A bargain four-pack will hold a mattress. It should not be the only thing between a loaded dirt bike and the car behind you. Look at the working load limit printed on the label, not the "breaking strength" on the packaging, and treat any strap with a nicked edge as garbage.
Ladders too. A flexing stepladder makes you tense, and a tense man on a ladder reaches sideways instead of climbing down and moving it.
Never cheap: the things that tell you the truth
Tape, square, level, marking knife. A combination square that isn't square is worse than no square, because you'll trust it.
Test any square you own in thirty seconds. Butt it against the factory edge of a sheet of plywood, draw a line, flip the square end for end on the same edge, draw again. Two lines on top of each other means it's true. Two lines forming a narrow V means the square is out by half that angle, and every miter you cut with it is wrong.
Levels get the same treatment. Set it on a surface, note where the bubble sits, spin it 180 degrees end for end, and set it in the same spot. The bubble should read identically. I've hung a door off a level that was out by a hair, and that door closed itself every time you let go of it. Took me a week to admit the level was the problem and not the hinges.
Buy one good four-foot level and one good torpedo level and be done for twenty years.
Never cheap: whatever's in your hand for three hours
Comfort isn't a luxury when the tool is doing the work through your palm. Diagonal cutters, linesman's pliers, wire strippers, a hand saw, a hammer.
Good pliers close all the way to the tip, cut clean instead of crushing, and spring back without you doing it. Cheap ones have a gap at the nose, so you end up cutting the same wire three times. After forty terminations your hand is done. This is where brands like Knipex justify themselves and it isn't about snobbery. The joint is machined instead of stamped, so it stays tight.
Hammers, buy once. A well-balanced 16 or 20 ounce claw hammer with a decent handle transfers less shock into your elbow, and the head stays on. A hardware-store special with a loose wooden handle is a genuine hazard.
Never cheap: the consumable, even on a cheap tool
This one saves people the most money and almost nobody does it.
A budget corded drill spinning a good brad-point bit will drill a cleaner, faster, more accurate hole than a premium drill spinning a bargain bit. Same with saw blades. A cheap circular saw with a decent 40-tooth blade cuts better than an expensive saw with the blade it came with, which is almost always a 24-tooth framing blade.
So: cheap machine, good cutting edge. Drill bits, spade bits, hole saws, saw blades, router bits, jigsaw blades. Cheap hole saws in particular are a special kind of misery. They wander, they burn, they glaze the teeth on the first piece of hardwood, and they turn a two-minute job into fifteen minutes of smoke.
Buy cheap without guilt
The tool you'll use twice. Bearing puller. Pipe wrench big enough for the main. Long-reach ball joint separator. If it comes out of the drawer once every three years, the cheap one will outlive you.
The tool you're about to abuse. Chisels for scraping paint or opening cans of sealant. Screwdrivers you'll use as pry bars, which you shouldn't, but you will. Keep a dedicated set of ugly ones and your good chisels stay sharp.
Clamps, in quantity. Six cheap F-clamps beat two excellent ones almost every time, because glue-ups are won by having enough hands. Upgrade later if a specific clamp keeps slipping.
Anything you might not actually need. Buy the cheap one first and let it tell you what the good one should be. If you wear out a $25 orbital sander, you now know exactly what annoyed you about it, and you'll buy the right replacement instead of the most expensive one. If it's still in the box in two years, you saved yourself $180.
Sawhorses, buckets, shop rags, work lights. Nobody has ever regretted a cheap bucket.
The trade-off I'll concede
Plenty of expensive tools are jewelry. A full set of Snap-on combination wrenches in a home garage is a nice thing to own and will not make one bolt come loose that a mid-price set wouldn't. Same with the premium European track saw for a man who builds two shelves a year. Ownership is a real pleasure and I'm not going to pretend otherwise, but be honest with yourself about which line item you're buying.
The one genuine exception on cordless: you're not buying tools, you're buying a battery platform. Pick one brand and stay in it. Three chargers and four incompatible battery types is how garages end up with nothing charged on a Saturday morning.
When the cheap one finally dies, don't throw it out straight away. Write LOANER on it with a paint pen and put it on the low shelf. Your brother-in-law is going to ask.
Wes Dunbar
Country & Skills
Grew up on an acreage and never quite left. Covers trucks, trades, land, and how to do the thing yourself.
