I'm in a similiar boat, only a year or so down the road. Here are the conclusions I came to.
Planes- buy used good planes that are relatively tuned up from trusted people. Not as cheap as big box stores but at least half of LN/LV prices
Saws - LV dovetail saw = great value. Other panel and tenon saws I"m picking up used older disston/atkins (good saws) and learning to sharpen them.
Chisels - LV chisels are great I bought an assortment of sizes I needed new and think they are well worth it. Looking at the Narex chisels for mortise work.
In general older tools are going to be better and possibly cheaper than what you find in Lowes/HD/Rockler/Woodcraft bargain price ranges.
One purchase helps keep HF in business, the other helps keep LV in business.
Those two outcomes have different values for me. - Chuck Nickerson