I found myself in this situaiton --looking for a laptop-- a few weeks ago.
Buying a computer with proprietary software --new or used-- supports people
involved in that business model. It's money that could support businesses
that are friendlier to our community.
We have to research so many aspects of compatibility before buying from a
non-free hardware distributors. That's because people who came before us
purchased from non-free hardware distributors. Just as we are doing here
today.
And finding a free-software compatible computer, from a proprietary
software/hardware vendor, is no assurance that you'll be able to find a
similarly free-software-friendly computer from them the next time you're in
the market for a computer. Supporting a free-hardware distributor is at
least some assurance of that.