I always kind of wonder how people stumble into this thread without ever hearing an ortho, or being interested in vintage headphones already. Like if you've already got your hands on the modern equivalent, I imagine that very few people are going to want to pick up the vint equivalent.... Rule 1 of Orthodynamics IMO is that the sound signature you're looking for probably already exists in another modern equivalent, or has to be teased out with mods. If you're not going in to it expecting to mod or dabble in modding, I don't see the point of starting here. That said, I think that planar magnetics have a really specific sound to them, a flat, low distortion response and generally a somewhat intimate soundstage with very detailed timbre. You can take an orthodynamic or planar magnetic driver and seriously tune it exactly to your tastes, because of how well the driver moves air, and how heavily the driver responds to differences in chassis.
As to the mentions of "how the yamahas sound," There's going to be a good amount of differentiation there, especially in the yh-3/hp-3 department. As I've heard, the lowest tier stuff had a high variability in driver quality, which is why they remain the cheapest to pick up. You might end up with something truly special, or just worth the price you paid for it. They are still a good deal, if you don't mind the looks.
I like my hp-1, unmodified they sound flat though edging toward dark more than bright, and have a roll-off towards the high notes. It's a smooth and enjoyable sort of flatness, though not everyone's cup of tea. The pair I modified with fiberglass tube insulation and dynamat sounds punchy and fun.
I do hate that prices are being driven up to such a ridiculous degree. The vintage versions should be seen as do it yourself projects, or used for learning/budget/collection purposes. Driving price for the sake of driving price just hurts everyone. I can't imagine the original t50 driver being worth more than an equivalently built Hifiman of similar design. There are examples of cans that are more like works of art than anything else, and I understand that sort of collectible pricing. Best example of that is the technics eah-830 and Sansui ss-100.
If I'm to be brutally honest about the money aspect though, I think that people shouldn't discuss worth here. And actually, since the forums changed at head-fi and less traffic goes through these old threads, the prices have started to fall in vintage across the board. I think that's great. Let people discover interesting things again without paying an arm and a leg for a piece of equipment that is probably 10 years older than the user themselves.