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The Thinkpad W520 is the last workstation version with the better keyboard and the speed to feel comparable to current laptops, and is what I currently use. You can find these for around $300-400 on eBay for 16GB of memory and a SSD drive. Lower if you choose to upgrade those features later. The main drawback is that the W520, and its heftier AC adapter, is heavy.

The question is how much battery life do you want. I get around 3 hours with an older battery. I can push out more with different settings.

The Thinkpad T520 is probably an option with better battery life, but I have no experience with it. It's likely also significantly lighter since I don't think it requires the larger AC adapter. I'd try the T520 if I wanted something more portable.

I'm currently running Ubuntu 14.04 and run Windows in a virtualbox with no issues. I've used this machine since 2015. I don't notice a performance difference between this and my older desktop (2010-ish, 16gb, i7) running Ubuntu 16.04.

Edited to add: If anyone from Lenovo sees this thread, I'm snap upgrading if the Thinkpad "retro" is released.

I work part time with a friend refurbishing retired business machines and re-selling them online. We get a LOT of Thinkpads obviously, but the T520 is an especially common machine and man is it awesome. Easy to clean, easy to repair, great Linux support, and built like a tank. Best of all, you can get a nice used one really cheap and throw in the max RAM and an SSD for under $300 total.

Edit: 2010~2011 era Thinkpads actually make great cheap Linux dev machines. If you want something a little smaller than the 15" T520, the T420 is great too. And if you want something "ultraportable" the X220 is a great choice and can be had for under $100 used on Ebay.

Yes Thinkpads are great, specially second hand ones.

Many companies tend to replace them after a few years so there are a lot of them on the market, and they are generally quite cheap.

Once thing to keep in mind however is the screen. At least for older ones, it tends to be bellow average (low resolution, low contrast, low fidelity colors, etc) as companies tend to "forget" to check the "good screen" option. It's obviously a generalization, there are some with good screens, but keep it in mind.

I'm the happy owner of an x61, upgraded with 4Go of RAM and an SSD, plus a new battery, it still going strong.

Personally, I'm always reluctant to pay a lot for a laptop. A laptop can, easily be stolen, fall one the floor, be damaged in any way. Cheap secondhand thinkpads fit my needs wonderfully in that regard. A few years ago, just 2 weeks after I bought my x61, I slipped on an ice patch, fall on it heavily and the screen was dead. I just bought another one, exactly the same, swapped the disk and I was good. It wasn't a big dent on my budget, it would have been a different story with a brand new Macbook Pro.

Other notes:

I've a thinkpad T460s (i7) at work, it tends to overheat a little, I would not recommend it. And there are a bunch of X1 carbons there to, they are not very reliable machines. Personally I would stick with the basic X2x0 or T4x0 models.

Thinkpads are really easy to repair, easy to disassemble and there are a lot spare parts on ebay (keyboards, battery...)

I couldn't find it again, but back in the day, there was a webpage which gives you the configuration details from the type number at the bottom, it was really convenient to get all the config beforehand from the seller, you just needed to ask in this type number. Don't know if it still exists.

I'm also using a W520, running Ubuntu 16.04, and it's working fine as a dev machine. Of course I stuffed it full of RAM and swapped in an SSD. I don't schlep it home very often, but it's nice to have the option.

I use the w520 w/ubuntu 17.04 and love it. 1TB SSD, 12GB ram I think... good times. Would recommend.

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