I'm probably in for about $20K in tools since the early 90's. The only tools I have that fit the extravagant bill would be the Lie-Nielsen planes and the Festool stuff I have. It's still a pretty modest investment with those.( I have more $$$$ hanging from the water pipes in the basement, in the form of bicycles, than I've spent on woodworking machines.
As for wood though, I do have a good amount of wood, and that's by choice. I'd rather have the raw material, ready to go, than have to source it when I need it. (I probably don't need anywhere near as much Cocobolo as I have.)
If I ever finish my kitchen, it along with the two baths, and library project, will have more than paid for what I have in tools and materials had I paid someone to do it. I also like the flexibility to adapt to a project in the middle and if necessary go in a different direction. Something that would be costly, and aggravating for them, if someone else did the work.
Everything is relative though.
"The first thing you need to know, will likely be the last thing you learn." (Unknown)