Starting fresh, knowing what i know now and how i work--and that a lot of tool repairs are not as complex as i still think...and assuming i've already got the sockets, screwdrivers, etc.
Starrett or B & S (even PEC) combination square (older is good) with 12", 18", 24" blades. (include protractor & center finder)
Plastic drafting squares--a 45 and a 30-60
Straight edge--minimum 24", maybe 36"
Incra Guaranteed square (or similar)
Bit & Blade cleaner (i use Trend--but whatever the brand the key is to use it)
(I've learned the value of set-up, without it--everything else is harder. Without good set-up tools, any other tool has the potential to be a boat anchor)
8" Jointer--wish i'd never bought the 6", it makes it tougher to "justify" trading up to an 8"
Dewalt DW735 Planer+Byrd head--that was my 3rd planer, and the Byrd completes it. (someday, maybe a 15" to get me close faster, then i'll use the 735 to finish)
Dewalt Radial Arm Saw--i'm becoming a believer in my GWI. Can do probably 2/3 of my cutting, and they are so far out of favor a first-rate saw can be cheaper than bottom of the line portable table saw. (be sure to get "How to Master the Radial Arm Saw" by Wally Kunkel)
Bosch 1617 EVSPK (with Bosch edge guide & template kit) and 10 essential router bits--95% of my routing. Slot cutter with various sized bushings would take care of a lot of the rest.
EZ-One table, about 110" of track & 8" Makita circular saw--almost all of the rest of my cutting.
Saw blades--i've accumulated an assortment of Amana, Tenryu GM, Forrest, Freud Industrial, Infinity, Popular Tools (Carbide Processor's secret weapon), and i change them often so that i'm using blades made for the task. Not to be a snob, but the only combination blade i own has never been opened.
Good chisels, glass plates, and sandpaper--to fix my "learning opportunities"
Good cordless drill/driver kit--coupled with good bits.
Band saw--another "cry once" tool.
That's it for the "big tools". Probably could get by with no table saw. Look at the list above and it's a lot of money--but i'm living proof that one can spend more than that (maybe a good bit more) and not be there!!