My approach to equipping a workshop is different than most. Although many of us have to start small for financial reasons, I believe it still makes sense to progress upwards from a simple level. If woodworking is worth doing, it must also be worth getting better at.
All this is why I recommend you buy the very best stuff available, even if it means going without certain tools initially. Although it wouldn’t be a disaster to spend $1000 on a whole bunch of inexpensive tools, what are you going to do when you’ve outgrown the capability of these tools and want to upgrade? You’ve now got to somehow get rid of the cheap stuff and replace it with something better. This isn’t easy and it’s always the most expensive way to go.
So what does all this boil down to? I favour starting with a good workbench and top quality hand tools – chisels, a couple of planes, a hammer, a few Japanese handsaws – stuff like that. You’ll be amazed at what you can accomplish when properly equipped. Build simple items at first, and then add the very best power tools you can – as you can afford to – in the order that makes the most sense for the work you’re interested in. Yes, this gets you off to a slower start, but what’s the rush? You’ll soon surpass the ‘buy-it-all-at-once’ folks who end up struggling with beginner tools that hold them back from getting better.