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Lee Valley (I'm sure you can get it elsewhere) sells a product called an Oops Arbor that allows you to mount two hole saws to a single arbor. The smaller one is held further out from the larger one allowing it to support itself as it drills.

I saw a video online, that suggested a simple jig that will allow you to drill straight into a relatively flat surface. Take a piece of stock that is square. From the end of the stock, cut a wedge section that is 90° in the wedge (the left inner face should be 90° from the right inner face) and the wedge vertex (the line in the middle of the removed ...

A drill guide will help you maintain the required angle, in your case, 90 degrees perpendicular to the desk. These are readily available at your local home improvement or tool store. Drill Guide http://www.homedepot.com/catalog/productImages/400/05/05534eb7-0230-4b1d-9f68-f9297f412a6f_400.jpg

In two words: Pilot hole If you have a drill with the handy leveling bubble, this can be handy. Otherwise line up your drill bit using something akin to a speed square or carpenters square (checking more than 1 axis), then drill your pilot hole. Not only is the pilot hole beneficial, but I find it makes your accustomed to what arrangement/direction you will ...

I have not seen the type of adjustable hole saw you describe, perhaps it's a regional thing (I'm on the west coast USA), but the type I'm familiar with have a spring loaded collar with "drive pins" that mate with holes in the bottom of the saw bit itself. I would buy mandrel like this: And a hole bit of the appropriate size which threads onto the collar ...

I saw an ad on a woodworking site and I was reminded of this question. These were touched on in other answers but I wanted to add something more concrete with a picture as an aid. The following is a picture of a drill guide. This would be used with your regular powered hand drill. You can see that the underside has 45 degree angle to as so you could also ...

You could drill as deep as the hole saw allows, then use a chisel to remove the "plug" left behind. Then drill again with the hole saw. One thing I would highly recommend anytime drilling using a hole saw is to give the chips a place to go. In this scenario I would drill a smaller hole using a spade/forstener bit inside the hole but overlapping ...

Just get it close to vertical, and add in a cable grommet. With these you can be about 1/8" off in the hole size, and angled like a drunken monkey drilled it, and it still looks great.

A forstner bit will result in a clean bottomed hole. Although 64mm is a slightly obscure size, you could expect a 64th of slop from a 2-1/2" bit. (Alternate choices include self-feeding bits, though you'll have to be careful they don't go too deep.) A hole saw would work as well, if you were willing to chisel out the waste. You could achieve a flat bottom ...

If you are unable to move the piece or provide additional access (as you describe), then another approach might be to cut a wood plug the same diameter as the current hole and glue it in place in the hole. Once it is set up you can begin drilling again using the larger bit.

Your diagram I think doesn't actually clarify the situation. I want to round off the corners of a rectangle with the curve starting 3/4" away from the corner If I'm reading this correctly 3/4" is your radius, so double that is the diameter of the bit you need to use. I don't think it's any more complicated than that. To place the centre point in ...

I was thinking about a hole saw attachment, however I do not think this will extract the wood if the depth does not exceed the total depth of the sleeper. That's correct, and in addition you could easily find it nearly impossible to withdraw the hole saw from the wood (for the same reason that it can be difficult to remove the plug from a hole saw when it ...

If you and can disassemble the piece and have a router with a rabbet bit, you can enlarge the hole by going around with depth set less than the full thickness of the material and the bearing against the edge of the hole. Then flip the piece over, attach a bottom-bearing flush-trim bit, and set the depth so it bears against the edge of the rabbet you just ...

Hole saw may not be the best tool for the task. A Forstner bit or something of that sort might be more appropriate. Even a spade bit might be a good choice depending on the material and the diameter of the hole.

One trick that will go (in this case) up to 5" is to drill as far as you can from one side, Drill a hole using the guide hole all the way through the wood, and then flip the board over using the guide hole to align the new cut from the opposite direction. they should meet up.

If you want the curve to start 3/4" away from the corner the radius of your curve is going to be 3/4". So, to make that curve with a drill bit, double the radius to get the diameter of the bit... 1-1/2" bit. It would be centered 3/4" away from each side.

I think I'd try making a guide block by drilling a through-hole into a piece of thick stock at the drill press. Use the same bit you plan to drill into your desk with. Next, locate the block on the desk where you want the hole (registration marks might help with this) and clamp or double-stick tape it in place. Use the hole in the block as a guide sleeve ...

Mount a bull's eye level on the back of the drill. Requires setup once. http://ideas.selfelected.com/2011/12/laser-and-level-for-drilling-in-right-angle/

Usually the cutting face of a hole saw is enough to give a good reference for verticality. If you're really concerned, google "portable drill guide" for some products that can help. This won't work well with hole saws, but if you're using a simple twist bit, auger bit, etc. you can put two squares on the desktop at 90° apart as a visual reference.

Three other options come to mind, none are perfect although # 3 is not bad. Toolmonger.com has very deep hole saw bits. (http://toolmonger.com/2009/08/14/extra-deep-hole-saw/) But damn, these babies are pricey and you may need a drill with horsepower! And good luck getting the wood block out of the drill if it wedges. You could cut the hole using multiple ...

With your 1.5" holesaw, cut a nice hole in a chunk of scrap plywood. Clamp this to the location of the old hole, and drill away. (Unless you plan to wrestle your desk to a drill press, the forstner will do you no good at all.)