I started woodworking in the summer of 2018 so I've only got about 4-1/2 years experience under me.

My advice is ask yourself what you want to make.  Small boxes, cutting boards, furniture, cabinetry?  The answer to that will help determine your starting path.  If you want to start small there is no reason you can't pick up some hand tools and some S4S lumber and get to work.  Those tools and skills are going to be transferable if/when you decide you want to make larger pieces.  And its not like you cant make larger pieces with hand tools if that's the route you choose.  Machines just make making things faster.

If you are like me and the answer to the question above is "D. All of the above" well that is going to get pricey...QUICK!  My advice for going down that road is DO NOT start with a jobsite saw unless that is your only option.  A used saw with any amount of cast iron on it is going to be a better choice.  I've seen people make some awesome things with jobsite saws but in my opinion they aren't worth the hassle if you can shop used.  If used isn't an option or prices are a nightmare, like where I live, then save up a tad more and get something like the Delta 36-725.  

A few other random thoughts:
  • Be patient and buy tools as you need them for each new project
  • Don't skimp on dust collection...I did at first and it was a very dumb mistake
  • If you are going to shop used tools keep a small amount of a slush fund available and always be on the lookout for a tool you may need.  There is no such thing as a used tool factory so you need to be able to buy when the deal is right.  
  • There is nothing wrong with having a hybrid shop.  In fact machines and hand tools are not mutually exclusive.  A good hand plane or 3 or 4 or how many ever  you want will come in handy even if you primarily use machines.  I still joint every board by hand.
  • Become a student of the craft.  Research and absorb information as if you need it to survive.

That's about all I have for now.