I have to emphasise that whatever tools you buy you really do need decent cutters/blades or you will become very frustrated.
As I live in the UK I guess you could say "how much would you spend £5000 on?" It's slightly more in real terms than the US or Canadian equivalent but for our purposes it would do.
I know that £5000 is a lot of money but in real terms the purchase of 1 or 2 high end tools could seriously erode that budget.
If you look at it this way you have to decide what sort of woodworking do you do?
If somebody makes items exclusively using hand tools, euphemistically called the Neanderthals (Woodtalk online "speak" - not me!), you may be able to buy the best hand tools that money can buy like a kid in a sweetshop (not sure what the North American equivalent is).
However if you are like me, a hybrid wood worker, about 2/3rds of the budget would be spent on power tools and the other on hand tools and you may well come up with a list like mine below:
Essential purchases in my kind of working are (in the case of large machines):
- a tablesaw with some top quality blades and a tenoning jig
- a jointer/planer
- a bandsaw with a selection of different good quality blades
- a router table c/w router and top quality cutter selection
- a spindle sander
- and the all-important dust collection system.
- a drill press is nice if your work involves the necessity to drill perpendicular holes. I have one.
- a selection of wood drills, Forstner bits, countersinks.
- a powered miter saw is nice but can be done with the crosscut miter gauge on the table saw
As far as hand power tools go:
- a couple of different size routers 1/2” and 1/4” collet size.
- a decent battery or mains drill.
- random orbit or sheet sanders
- a shop vac
- Measuring/marking out equipment
- Workbench with vise(s)
- Various specialist luthier tools (essential for me)
- Hand plane selection (#3 to #7)
- Specialist hand planes (plow plane, router plane etc)
- Clamps, clamps, clamps. Did I mention clamps?
- Personal safety equipment (eye, ear, respiratory protection) for you and any visitors
- Storage Cabinets/Shelving
- Lumber Storage
- Decent lighting
- Air cleaner
- Spray system for finishing
- A sharpening system of some kind
- A flat assembly table
- Some form of audio entertainment
- A fridge for the cold beverages
- A padlock on the shop to lock all your goodies away from prying eyes