There is a very easy way to keep XP up to date with the latst security fixes - just get your wallet out!
The UK National Health Service has done just that - paid Micro$oft millions for ongoing security updates for another year or two. i.e. I am paying my taxes for universal health care (a good thing IMHO) only to see it lining Bill Gates' pocket rather than treating patients. If BG wants to be considered a 'charitable benefactor' then hows about not taking the money from such causes in the first place!
So yes, planned obsolescence for sure - there is no technical reason that XP cannot continue to be upgraded to keep it "secure", because it is being done as we speak!
As far as "the weakest link" is concerned - that has little to do with your OS, IMHO. The idea of "hackers"** as genius-level super-programmer 007-villains is mostly a distortion to make people wet their pants and get their wallets out - the "weakest link" is usually the bag of flesh and blood sat in front of the monitor, and most of the biggest security breaches come from social-engineering rather than any kind of clever programming.
And I strongly agree with Krisidious - having almost every app' and background task these days punching holes in your firewall, often without you even knowing it, is a massive source of possible 'exploits' for the genuinely technical security breaches. Very little software is upgraded so regularly that it needs a permanent connection, and I am perfectly able to spend a few hours on my PC without checking how "popular" I am, or needing to see a silly cat video! (must 'fess, I do find them rather addictive though!).
Call me old-fashioned, but if I'm not browsing/downloading, the router gets turned off at the wall. If an app' won't play nicely with that, it goes in the bin - simple as that!
*(*PS - apologies to any real hackers out there. As any true hacker knows, a hacker is someone who just loves finding new ways to make computers do the 'impossible'.
There's another word for the 'naughty people' we're talking about here - "criminals".)