Quite the rookie myself. So far, though, I've only had to buy one saw blade, a few brass brushes, a couple of wire wheels, some evapo-rust, and a whole bunch of WD-40. I've gone sweat-equity the whole way, partly out of personal inclination, partly due to being broke. $1000's a fortune! You can do SO MUCH with that!
I'm not even being sarcastic. Well… maybe only a little.
My best advice, one rookie (on a tight budget) to another? Go slow. Do your due diligence. Research. And ask for advice whenever you can, as much as you can, because ten minutes with someone who knows what they're doing will save you a whole night of research. But then research that. Because there's another expert who has an entirely different technique for doing the same thing, and that one might work better for you. In the end, really understanding what you're doing is going to carry you a lot further than any tool, or any shop's worth of tools, for that matter.
So I can't really tell you what to spend your money on, but I can share a few of my thoughts and experiences in equipping my shop on a very small budget. First off: restoring old beat-up tools is a freakin' hassle, takes forever, you have to do more reading than you ever imagined… but when you're done, jeez, you feel like a little machine god, and most importantly, you understand the thing through and through. You know those stories, about the old-timer who could fix anything with duct-tape, spit, and curses? It's because he understands what he's working on. And it's not just fixing: if all you ever do with tool is what it says on the box, you're missing out on the possibilities and you're missing out on getting the absolute most out of the machine.
Second, if you're anything like me, your imagination can get away from you, and you find yourself wanting to buy tools that you don't even know how to use, or what they're for… keep your feet on the ground, and concentrate on what's in front of you. Know where you're at.
Third: always read the safety instructions. Look up any unfamiliar words. Read them again. Chant them, under your breath, as you use your new TS/BS/RAS.
If for now you're just interested in outdoor furniture and shop benches for now, you might want to consider a radial arm saw. They can be had cheap as hell (I see them for $50 on Craigslist all the time) and they can do A LOT. They're tricky machines, though. Tricky, in my opinion, because modern consumers don't want to have to learn, they just want to "plug and play." If you're willing to learn, though, you can achieve the functionality of a whole host of machines for $50 bucks, and some sweat equity. And you'll learn a heck of a lot about machines working on one of those things. But my point here is not to recommend the RAS, so much as to point out that there's a lot of ways to skin a cat, when it comes to making things out of wood, so don't get locked in to one equipment route or another.
People built stuff out of wood for a long, long time without a table saw. Heck, they used to do it with sharp rocks.