I think you are wise to consider spending 1/2 now on core items, and have money to get things you need as you need.
Sounds like you want or feel you need the Table saw. I have a contractor saw, and it works well for now, but I want a Cabinet saw bad. For the TS, I'd vote for the Griz 1023. Get the one with the cast iron router table and you'll have 2 tools in one to start with. When you feel you need a different set up for the router table later, the CI one will still work great for the extension table. 1200.00 shipped
Sounds like you will be working with raw wood. Jointer and planer will be a must. Find the best deal you can for these. Lots of people like the Griz 4090 8". Usually priced around 942.00 shipped. That wouldn't leave much room for a planer except for a lunchbox unit. Lots of people like the DeWalts and the Delta. I got the Delta unit on a great sale at Lowes a few years back. Never been plugged in. I'm building a mobile cabinet for it now. Those three items will put you at 2500.00. Note, I don't own any of the Griz tools at this point. My suggestions are from what I've read from owners who are happy with them. I am considering a 1023 myself if something used doesn't appear around the time I'm ready to upgrade. And there is nothing wrong with other brands for these items. Griz just seems to offer a lot of bang for the buck, and a good rep on their newer tools.
One thing I will add is to get some good set up tools. No matter what you spend on the core tools, they won't be worth squat if you can't set them up right. You need to get a good dial indicator and a good set up square, minimum. I just recently purchased these, and setting up the equipment right is all the difference in the world.
Good luck! Watch the Craigs list, Ebay for tools in your area you can go look at, the classifieds here and on other wood forums. If you purchase in the near future, many people are getting some nice rebates from Microsoft for using the buy now option on qualified purchases. If inclined, look at some government auctions in your area. I know there were some here in TX recently. Houston and San Antonio. Schools that were getting rid of some woodworking equipment. Might find a good deal there. And keep an eye out in the local paper even. Like you, I'm not real comfortable purchasing used, in case I miss something that is a problem. If you can make friends with a local woodworker that has an eye for these things, he/she might be willing to help if you find something interesting. Jim.
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