I can't really give a great answer to your question - I'm still learning how to deal with woodworking on a limited budget myself, but I'm getting there. It's not always easy, but when I want something I can't afford, I am starting to remind myself more and more that someday my day will come when hopefully there will be more room in the budget for my woodworking hobby. I'm also hoping to start selling the occasional item within the next year to help bring in some extra money for woodworking related expenses.
I could not consider a 12" jointer, given that the equipment had to be moved down the stairs to my basement, and the cost would blow my budget. What I wanted in an 8" jointer was true tables, a fence that is solid and easy to adjust, a cut depth gauge that is reliable, and long tables that aid in flat­tening longer bowed planks. I have found that the Taiwanese tools have come a long way in the past 20 years. I purchased the King KC-80FX 8-inch jointer, with lever adjust parallelo­gram tables. The system arrived in a good state of tune, and the well-written manual includes a full parts list and exploded parts diagrams. The tables were extremely heavy; more about getting things down the stairs later. The jointer is reasonably priced, it runs smoothly and it is well made.
I went out and bought a dovetail pull saw for some of the finer cuts that I needed to make. I’m sure I’ve used this a few times on previous blog posts. It is great for the smaller cuts, and I’ve even used it to cut some larger pieces when my bigger saw didn’t fit. The combination of the dovetail pull saw and the push saw works fine, and isn’t too terribly expensive, but I’ve found something even cheaper that works just as well.
The level of sophistication in a $250 shop is significantly less than a $2,500 shop.  But keep in mind even a $2,500 budget is entry level.  Acquiring a shop full of the perfect tools for each and every job takes a life time.  But that doesn't mean that producing quality work takes a lifetime.  One of the most enjoyable aspects of this hobby is the constant need to solve problems in order to produce good work.

I wouldn’t give up on Craigslist or garage sales.. For around $1K or less, you can pretty easily find the four big ticket items (TS, BS, Jointer and Planer) and have the extra $2K to spend on accessories, material, DC, other goodies, etc. The key is patience and persistence, and if applied correctly, you can have a fantastic setup for very little compared to purchasing new. If you are setting up a business, you don’t usually have the time to scour for good deals, but for a personal shop, there is no pressing need other than that itch to get something done.
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