My approach is somewhat different. I will grab anything at a swap meet that seems like good value (translate to free if I am really lucky) and not much care if I can use it. In time, after getting it working and putting it through its paces, I can decide its fate.
As a result I have an enviable selection of high end test gear on the work bench and in the closet and on the shelves that cost me nearly nothing but would have run many tens of thousands of dollars to purchase at listed prices. And many items good for swapping fodder.
The big benefit of this method is that I gain perspective and experience with this gear. I see what it can do and one day I remember I have it and will trot it out for use. My Q meters are a good example. Lots of power supplies. I am down to only five oscilloscopes now. Lots of probes, voltmeters, signal generators, VNAs, spectrum analyzers, bridges, the list goes on.
Then of course we can get into tools. Soldering equipment, hand tools, power tools, vises, clamps, saws, and so on.
So my advice is not to blow a few hundred on something you aren't sure you need. Just accumulate and then see what you have.