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I'd find a used 6" jointer, buy a refurbished lunchbox planer, and get a Grizzly contractors saw. I bet you could do it all for around $1K if you looked for some deals.
TS $500
planer $300
Jointer used $250
Of course, these won't be the best tools money can buy......but you can make some darn nice furniture etc, with them.
I've been functioning with a Craftsman lightweight contractors saw with a redone motor for awhile now with decent results. Surely, that Griz TS is a much better and more accurate unit for $500. Hell, I don't even have a power planer. Unless you count my arms and a jack plane a "power planer".
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Jeff, on the saw side, one of the hybrids would actually be an excellent choice for you to upgrade given your power situation. No disadvantages over what you are used to and the current crop of them is pretty nice in the way of features.
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Jeff,
Just today I saw the powermatic contractor saw on sale for $399. If I were in the market I'd buy it. That'll still leave you enough room for a good used planer and joiner.
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I'd go TS first, then jointer later. A TS IMHO is used throughout almost ALL projects, A jointer only in the prepping stage. I did w/out a jointer for many years but it helps much on accurate milling...
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As a follow up.......
It's really darn hard to do fine woodworking without the benefit of squared boards. You name the project and squared lumber is the key to making everything fit and look fantastic. For this reason, I really recommend trying to get all three tools for $1000 as it is very possible. As others have stated, even the Powermatic contractor's saw is $400. Lord knows, that is three times the TS I have now. With $600 to spare, you EASILY can get your hands on a used 6" jointer and a quality lunchbox planer (higher Delta, Dewalt, Hitachi, Makita, etc.)
With these three tools, you'd be hard pressed not do some darn good woodworking.
If you have the desire, by the way, there are some nice jigs you can make to convert your planer into a jointer. I personally don't like the idea, but others rave about it. You can probably Google it and find the jig....or get an internet subscription to finewoodworking.com and see firsthand via video on how to make it.
Either way, $1000 will get you well on your way to creating great work.