Wow, thanks everyone for all the great info. You must all see a million people asking these questions so I'm doubly thankful for your patience. After reading all the above, here is what I'm now thinking:
Lower end table saw than first planned (grizzly or Jet?). I'd still like to get a 3HP saw as i think I'll really enjoy working with harder wood. I have no shortage of 240v plugs in my space so that's no worry.
Band Saw (need to start researching these now)
A selection of
hand planes- spring for high quality new ones
Sharpening stuff
A couple of
hand saws. (I've already used the Japanese ones a little so I know how nice they are but need to do additional research)
Small tools (marking gauges, etc- i already have various squares etc)
Adapters to fit my shop vac to the machines (upgrade to real dust collection later)
A set of good
chisels and mallets
A
drill Press (I already have a few different drills but nothing for precision drilling- probably wait on this a little)
I'll buy all this in the order that I need it, of course.
Projects in order I need to complete them:
1. Finish off a kayak (i can do this on saw horses with stuff I already own)
2. Build some mobile work benches (not wood working benches) for the shop. Maybe try to build them with small height adjustments so they could double as out-feed tables etc
3. Build a prototype of an art "door" that I have in mind. Basically a miniature door, distressed and "aged" with large vintage style peep hole, containing a scratched lens, some images and a flickering backlight to be mounted on a gallery wall.
4. A real woodworking bench- I like the look of the split top roubo ones I've seen but have no idea if I would benefit from something this elaborate
5. Fencing and wood cladding- i have various concrete walls and older fences on my property I want to either face with nice wood (rather than plain pressure treated stuff) or replace entirely. I hate chain link fencing and I have tons of it. I have the tools for this work already though.
6. dining room table
Anyone want to suggest a project or two that I can use to starting adding to my skill set but that won't be too costly or worry producing if I waste a bunch of wood?