Ok, the leap from $1,000 to $2,500 is a big one.  I certainly didn't make it at one time.  It took me years.  But I know folks that decided they wanted to get into woodworking and dropped at least $2,500 getting themselves outfitted.  When you do make the jump, the thought process becomes much less about making sure you can get the job done and becomes more about having quality tools to get the job done.
I use a 9″ x 12″ Chinese grade B surface plate and wet the back of the carborundum “sandpaper” to hold it in place. Obviously not the “budget” version, but I have the surface plate for other purposes. At about $17 from ENCO it wasn’t very expensive. And it *really* is flat to better than 0.001″. So the thickness of the paper is the biggest error. I also have a good assortment of Arkansas and other types of stones, though none of the Japanese waterstones. I generally don’t use the surface plate unless the edge is really bad e.g. an abused tool picked up at a yard sale.
Over a year ago, I wrote up a round-up of three woodworking resources Learn To Build Your Own Furniture With These Impressive Carpentry & Woodworking Resources Learn To Build Your Own Furniture With These Impressive Carpentry & Woodworking Resources Few things are as satisfying and relaxing as making something new with your own hands. Programming comes close, at least for me (and I've recently offered some tips on learning to code), but it's still... Read More which included talented YouTube woodworkers Matthias Wandel, Steve Ramsey, and Marc Spagnuolo, AKA The Wood Whisperer. All three still produce wonderful work — and today I’d like to introduce you to five other YouTube woodworking channels worth following.
My shop ended up being 23 x 19 feet, for a total of 437 square feet. I put my wood rack in the basement, but out­side the walled in shop area. To keep the dust in the shop, a three part strategy was employed. I have a dust collection system, an air filtration system and a shop vacuum for cleaning dust out of machinery. I put up new walls, installed new electrical service, lighting, and two access doors for ease of materials move­ment. The shop includes two windows so that I can enjoy natural light, and not feel like I am squirreled away in the basement.

That just reminded me of a FWW piece many years ago that had me rolling on the floor.  Craftsman had built a large piece being delivered to an apartment on the top floor.  Couldn't get it on the elevator so they got controll of the elevator and ran the top of it to be even with the floor, loaded the piece on the top of the car and rode with it inside the shaft while balancing it and keeping it from hitting the shaft walls.  At some point in the trip up they lost control of the elevator and it started making trips up and down to other floors.  I'll see if I can find it.
The type of wood you choose will determine the overall strength, look and cost of the finished piece. Many varieties of wood exist, and CZ Woodworking will work with each customer to determine what wood will fit your needs best. Each wood has its benefits and can be utilized in a number of different ways to create various looks within a project. Explore the various samples below to determine what might work best for you.
I, too, would pass on the Jawhorse, and agree with the suggestion of a solid bench. (Remember, it can double as a desk if space is limited.)  A used solid-core door can be a starting point, but there are better options, such as laminating your own from scrounged 2x4s. Spending time at flea markets looking for old tools that can be reconditioned is a good suggestion, too.
I just do it. Lol. Most of my projects are for my wife so its easier to scrape money together then listen to complaints about them not getting done! Seriously though, its tough. I have two expensive hobbies......woodworking and bass fishing, latter of the two being the worst. I reserve all my side work money for the two. One thing that helps is owning our own saw mill, lumber is basically free other then time.
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Oak is one of the most widely used and respected hardwoods in furniture making. Available in two varieties — red and white — oak is very strong and also quite heavy. White oak is sometimes preferred for furniture making because it has a slightly more attractive figure than red oak, but either variety can give you a beautiful finish that stains very well. Oak can be used for almost any woodworking purpose, and is an excellent choice for pieces that will last a lifetime – literally! As they say, it is “solid as oak”!
Low-tech tools are high on value A basic set of handplanes lets you true edges, flatten panels or wide boards, and achieve finish-ready surfaces. Start with a small cluster of handplanes—low-angle and standard block planes, a No. 4 or 4-1/2 bench plane, and a jointer plane. A set of inexpensive chisels is essential for chopping, paring, and trimming.
Steve Ramsey makes woodworking fun. His YouTube Channel, Woodworking For Mere Mortals Building, shows Steve making cool stuff in his garage in Marin County, California. From games and toys to special holiday projects during his 12 days of "Craftmas" (wooden snowflakes!), Steve consistently puts out new DIY woodworking videos and projects every Friday.
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Rob Cosman and Paul Sellers. Rob is damn near a genius when it comes to woodworking. He routinely comes up with methods and tools that sort of change the way we all do things in the shop. The guy is also an amazing instructor. Paul Sellers is also an amazing instructor. These are the kinds of guys that all the rest on your list learned how to woodwork from!
I, too, would pass on the Jawhorse, and agree with the suggestion of a solid bench. (Remember, it can double as a desk if space is limited.)  A used solid-core door can be a starting point, but there are better options, such as laminating your own from scrounged 2x4s. Spending time at flea markets looking for old tools that can be reconditioned is a good suggestion, too.

Low-tech tools are high on value A basic set of handplanes lets you true edges, flatten panels or wide boards, and achieve finish-ready surfaces. Start with a small cluster of handplanes—low-angle and standard block planes, a No. 4 or 4-1/2 bench plane, and a jointer plane. A set of inexpensive chisels is essential for chopping, paring, and trimming.
I have been around woodworking my entire life.  I have always been intrigued by how you can take something like lumber and turn it into a wonderful, beautiful piece of furniture.  Once I graduated high school, I kind of got out of woodworking.  I wanted to go a different route.  I was going to college and just trying to make ends meet on the bills.
Ebates.com - Ebates is something I'll check after I've already found a deal that I'm going to bite on.  The rewards aren't usually good enough to compel me to purchase on their own.  But if you get an extra 3-5% cash back over your entire $250 budget, it can add up to an extra hand tool for doing nothing more than using their link to an online store.

The best advise I can give you is to get and read the book "Hand Tool Essentials" by the staff of Popular Woodworking before buying any tools.  It is sort of an inexpensive crash course in hand tools.  Chris Schwarz's book "The Anachrist's Toolchest" is another good source of information on handtools that I found to be a fun read.  Use the internet to learn all you can about a tool before buying.  The tools you need are dictated by what you want to build.
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