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Well, it sounds like you have a lot of the tools already to at least get your foot in the door.My initial plan is mostly small stuff. I was sorta thinking about trying to build organically to some degree. E.g. building and finishing some blanket ladders (which should be cheap and easy), selling them (I've got loads of marketing experience) then dropping the margin right back into more tools. At least that's the way I'm thinking about it right now. I also have some personal projects I want to do like a farmhouse kitchen table, cutting board, a desktop for my office, an aquarium stand, etc. But I definitely want to approach this very incrementally.
Edit - Just want to give some clarity here. I've accumulated a LOT of hobbies over the years. I tend to get bored really quick. For example, once I hit that 80% mark of competence, I'm basically done. And that usually tends to happen very quickly. I don't want to spend a couple grand until I'm fairly confident that this is something I'll want to do long term. Hence the "make me work for it" strategy around buying new tools. If that makes any sense at all.