While I enjoy the history and story behind estate pipes, I find that significantly old pipes (70’s and older) are likely to have been abused. I’ve bought a few newer pipes, less than 5 years old, that are gorgeous but beat to absolute shit. The bowls are over-reamed, rims charred, airways charred...
I won’t knock estates outright, because I have a few that are absolute treasures. But, in my experience, my best smokes are from pipes that I’ve properly cared for. I don’t char rims, I clean after every smoke, etc.
If the price is right and it’s been lightly used, I say go for it. Otherwise, I’d rather pay a little bit more for a new pipe. Just my personal opinion. I just bought a 60’s Dunhill recently that looks fairly clean, but needed 50 pipe cleaners soaked in alcohol, coffee grounds in the bowl, and still tastes like crap. Estates can make for disappointing smokes, I’d says it’s 50/50.