I recently went though a similar exercise. If I had to do it again, here is what I'd do:
1. Planes: Nice, pre-war Stanley #5 plus a Hock or Veritas replacement blade and chip breaker and a Lie-Neilsen block plane (either one). The old Stanley will teach you how to properly set up a plane.....a good thing.
2. Chisels: set of Ashley Iles chisels from Tools for Woodworking. Amazing for the price. Maybe a 1/4" and a 3/8" mortise chisel also.
3. Saws: Get old Disston cross cut and rip saws and a Disston tenon saw. Have Mark at Bad Axe sharpen them or to it yourself. I did my own for the full size saws and Mark did my tenon saw. They all work well. I also bought the Bad Axe small tenon saw that is a nice dovetail saw.....my only real crazy splurge but worth it. I suspect the much less expensive Lie Neilsen works every bit as well. Make bench hooks or buy a set from Mark.
4. Measuring and marking: Get a digital caliper...a cheap one is fine. A stainless steel ruler from an art store is nice. Get a couple of machinists squares from someplace like McMaster Carr. They are accurate and not terribly expensive. For marking, I bought a Tite-Mark marking gauge. I wasted my money on the Lee Valley and a wood one. Spring for the Tite-Mark.
5. Drilling: Stick with a cordless electric. I've had a hard time finding a decent eggbeater drill. A brace is cheap, but make sure you find a decent set of bits and a file to sharpen them with.
6. Router plane: Find a decent used one or get a Veritas or Lie Neilsen. I found a Millers Falls for $30 and it works fine.....although someone painted it with what looks like Navy surplus paint.
6. Sharpening: get a set of oil or water stones and learn how to use them. For the coarse stone, I'd get a diamond stone simply because a coarse waterstone wears so quickly...it is also handy to flatten waterstones. You'll soon be sharpening everything in the house. You really don't need a sharpening jig, but it is handy to use sometimes.
7. With the rest of the money, but wood and make stuff starting with a nice workbench. I made Will Meyer's Morovian bench. It isn't as heavy as the Roubo but it is plenty sturdy and heavy enough.
Don't go crazy and spend all the money at once. Used tools are bargains as long as you are willing to put in the time and effort to tune them up. Personally, I like doing that.