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This is my experience buying (and advising others regarding) old thinkpads on ebay.
why a thinkpad?
Because they are durable and well-supported by Linux.
Many other specific laptop models fit these two criteria, but the thinkpad line is the most common one that many people (myself included) think of that generically fits this description.
Because the selection on craigslist is not good in most areas, and prices on amazon are way too high.
In particular there are a bunch of sellers on ebay that seem to be e-waste recyclers or business liquidating old business-grade hardware, and the like.
which one to get
basic description of the kinds
There are three serieses that I have paid attention to: X2?0, T4?0, and T5?0.
These are 12, 14, and 15.6 inch respectively.
The '?' there is to indicate what model year it is. The '?'=3 year is 2012, i.e., the X230 was release in 2012. Because obviously that makes the most sense.
I've got a X230 that I'm happy with.
I think I paid $70 for it on eBay shipped, and added a SSD and charger (eBay listing didn't have one) for a total cost of $110.
I've got xubuntu Linux on it, and it's fast enough for light duty web browsing and programming.
I don't know that it would be very fast in Windows though.
My main reason for getting one that old was because the newer ones don't have as good a keyboard, IMHO.
You might be able to find a newer one for cheap, maybe x250 or newer.
I particularly like the size of the x2?0 series (12 inch display).
my other thinkpads
I have had a T450s since college.
It's got space for like 3 or 4 SSDs, depending on how you count them I think, which is cool.
Also it maxes out at 20GB ram.
The extended battery wedges up the keyboard on a tilt, which is handy.
14 inches is a good size, but not super portable.
The keyboard is pretty good, but not quite as good as my X230.
I use a T570 at work (I think. I can never remember).
As a laptop, I kind of hate it. (I usually use it with a dock, though, so work is tolerable.)
15 inches is just too big, and the keyboard is off-center since it has a numeric pad, so typing takes a lot of learning.
Also, the keyboard is noticeably bad.
Even as far as laptop keyboards go, it's not ver good.
It is mushy and bendy and infuriating to type on.
what get stock vs what to upgrade
Get one with a battery, since those are expensive and knockoffs are questionably safe. But without a charger, because those are cheap and knockoffs are fine
Also get an SSD. They're always getting cheaper, so probably best to get a thinkpad with no HDD at all and install one. Usually that also means it won't have a HDD caddy bracket thingy, but SSDs are not fragile so some cardboard or tape or whatever is fine
Same is true with RAM, to a slightly lesser $$ extent. And ram is not quite as universally compatible, so check compatibility first
things to avoid
X240, T440, T540, etc. That generation had a weird touchpad that everyone hates.
(Later models, including my T450s, went with something more like the old style. So yes, that counts as a mistake, and should be avoided!)
Anything with a BIOS password on it.
make sure it doesn't have a BIOS password!
Yes, I just said this in 'Things to avoid', but it's so important that it bears repeating.
Last time I checked, there is no way to remove a thinkad bios password, short of desoldering the security chip and soldering a new one.
And that's not at all easy, and probably won't work on newer ones.
So make sure to ask the seller to confirm that there is no BIOS password.
If you do unfortunately end up with a BIOS-locked thinkpad, that should be good enough reason in itself to return it.
That definitely counts as "not as described" (even if the listing description didn't specifically mention it).