The benefit of Macs is that they're high-end unix workstations optimized for usability. As far as I know Apple is the only company still making anything by that description.
I do not find Macs to be very "usable", and previous-gen ThinkPads outranked them in everything but the shiny-showing-off-at-starbucks metric. However, in the last generations, Lenovo has nerfed the ThinkPads (new ones don't even have a middle mouse area - no more buttons, either).
They've also even put the logo upside down so that you can show it off at cafes.
Is there a Thinkpad model you would recommend for day-to-day use (mainly Java programming and LaTeX writing), that is light enough to be carried around daily?
Ihe UX of OSX is not that of a high end unix workstation. High end unix workstations do not need homebrew. High end unix workstations do not provide the miserable, second class Xwindows experience that is found on OSX.
So I used "high end unix workstations" for years and years and years and OSX isn't perfect, but jesus christ I'd take its UI over just about any of the UIs from its competitors.
(and remember trying to compile anything on sunos and only having suncc? fuck that, imo, I'll deal with xcode)
It's not that they "hold their value", which implies they'd sell for something similar to the original purchase price, and that's crazy. Rather it's that their value drops considerably more slowly than the average computer. A 3-year-old Mac is still worth only a fraction of the original purchase price, but a typical computer is worth only a fraction of that fraction.
Anecdotally confirming. When shopping around for the past 10 years, I've usually bought used PCs and used parts, both desktops and laptops, but after deciding to try out a Mac in early 2012, buying used just didn't seem to be worth the discount.
It doesn't seem to be so bad right now, but part of this may be due to my insistence on getting at least 4GB of RAM for a MacBook Air, which was hard to find on the used market.
Adding to the anecdotes[1], of the last 5 computers that I have owned, 0/2 of the Macs are still running, compared to 2/3 of the non-macs. Because of this, I refuse to ever purchase a used mac, the discount is not worth the risk, especially considering the fact that it's nearly impossible to repair them on your own.
[1]Random idea for a website/service: Computer reliability statistics by model/year. Could be really useful for people in the market for used machines. Not sure how/where you would get the data though. Seems like forums are overrun with anecdotes, but actual data is few and far between.
Macs are quite variable in terms of good models and bad models. This seems to apply to both laptops and desktops. Unfortunately. I also haven't heard of a website or service that has the reliability statistics you want.
You didn't mention Applecare. It is transferable and is for 3 years. So if you buy a 1 y/o machine from a hipster who wants to upgrade, you would be covered for the remaining time.