A dilemma for sure. However, I think there is likely a consensus that for most people on a budget of sorts, it doesn't make sense to buy a new boat (high initial cost, depreciation, needing to add equipment to customize it for your own needs, etc.). Also, it doesn't make sense unless you have real skills in repair to buy a real old "project" boat that will require immense time and unknown resources to bring it back to good shape--and even then you often end up with a less than great boat.
For most of us, I suggest it's most reasonable to buy the boat that we can afford, and is in as good shape as possible, and meets our specifications for the kind of sailing we plan to do.
Just my thoughts...