All in my small 2 car garage only taking up one side I've got the following and don't regret any of the purchases. I will admit with 2 kids and a few other hobbies, I don't get in there very often and a simple project like a humidor takes months because I don't want to get started unless I can spare 4 hours .

Table Saw: 1st purchase. I have a Used Sawstop 3hp Professional Cabinet Saw. It's pricey, but I found it used and it made the level of my projects skyrocket. Super accurate, clean with dust collection, safe. etc..

Planer: 2nd Purchase. Currently have a 13" Lunchbox Dewalt. It works verywell and I can't justify a full 15"+ standalone unit. Absolutely necessary to build things and not be limited to designing within dimensions of store-bought lumber.

Dust Collection: 3rd Purchase. Need it with a jointer and it will make everything else work better. Have a used Jet 1.5 HP unit I got when I bought the table saw. It's not the best system in the world, and I'm not super anal about setting up every cut to get every spec of dust. I have the table saw hard-piped in and one 4" flex hose for the other tools. It keeps me from being ankle deep in sawdust.

Bandsaw: 4th purchase. If you have a jointer and planer, I'd recommend getting a larger bandsaw. You can save a lot of wood by resawing. No need to turn 50% of a 2" board into sawdust just because you needed a 1" part. Plus there are other obvious uses.

Jointer: 5th purchase. If you are using rough lumber, it's almost necessary. I got by with just a planer and some jigs so that's why it's a little far down. But infinitely faster to get the job done right with a jointer. I'd only get it if I were getting an 8" full size system. I have a used Grizzly with a helical head.

Track Saw: 6th Purchase. This was my first jump into expensive tools and I got a Festool. Many more options out there now. With the full size table saw w/ outfeed, I don't need it as much. But there are times that you can get finish quality that is way harder to get with any other tool. This isn't quite the same investment as the other tools, so can maybe slide this in between somewhere too.

Router Table: 7th purchase. I stopped short of splurging on this, then haven't had as much time. But it's the next thing I'd add. Helps with a lot of the work. I have a router plate built into my outfeed table, but it's not the same quick adjustment and dust collection you can get from a dedicated table.

Drill press: 8th purchase. Admittedly I have a terrible hand-me-down Harbor Freight contertop press. But I find myself using this the least.