For reference, I live in a small town along the Hudson River on the edge of the Adirondack Mountains in upstate NY, but have worked for Boston and NYC startups

For reference, I live in a small town along the Hudson River on the edge of the Adirondack Mountains in upstate NY, but have worked for Boston and NYC startups for some time now. So, not living near a top 5 city doesn't really have any bearing on the conversation. I agree that long-term contract-to-hire is a reasonable way to go for may employers and employees, particularly folks that already are already contractors, but the premise of "you've got a couple weeks to prove yourself" is a non-starter. I'm not going to quit my day job and risk my family's financial security for a company that is unwilling to take a similar risk on me. In an ideal world, it is the best way to evaluate a candidate. However, if it were practical, it would have already become an industry practice. The fact that it seems to be rare indicates to me that it does not work very well. As a Systems Engineer, a practice that I would like to see more of (and may try to implement at the company I work for) is a brief troubleshooting exercise with a shared tmux session. Set up a server with some problem and ask the candidate to identify the issue and try to resolve it.