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I can count programs that were really broken on one hand between windows versions, let alone between minor updates.
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@Katsunami ↑ ↑ ↑ +1
For Windows 7 and 10, I can't recall any monthly update ever breaking anything. Nor did I get any breakages when I went from 7 to 10, I skipped 8 and 9 (aka 8.1). I can't remember what XP was like in this regard, but I do remember applications it would crash far more often than they do now, and BSOD's were quite common. I did think I had a problem with a 3rd party product when I upgraded W10 1709 to 1803, but it was false-alarm/red-herring.
XP broke many old programs, mostly because they exploited "Undocumented Features" that were promoted by certain Windows 'gurus' as a means of selling their books.
Vista broke some more, such as anything that used Column Handlers, the so-called replacement is Property Handlers. Rumour has it that when asked about backwards compatibility, a certain senior MS exec replied "What's that?" My old Toshiba Portégé came with Vista, which is the one of the reasons I decided not to put it on my desktop.
I have had to replace software because it interfered with other 3rd party applications, mainly shell extensions. Qt based applications seem to be ultra-sensitive to 'poorly written shell extensions'. In most instances I've been able to find and switch to a 'better written' alternative without much drama. An exception was an abandoned swiss-army-knife package. I could find plenty of replacements for the features I used, except clipboard management. Eventually, like several years, the Clipboard Fusion developers added features to their product that matched the particular things I liked about the old one - so I was able to ditch the rusty knife.
In my experience browser updates are much more likely to break 3rd party software (extensions, etc) than OS updates. I'm still running Firefox 54 because of Mozilla's deprecation of extensions. Occasionally I run across a site that has problems on FF 54 (eg UK Telegraph), or an updated extension has problems on FF 54 (eg Lastpass). My perception is that my FF 54 with its plethora of add-ons is faster than the latest Chrome with very few add-ons. If I could get add-ons for Edge similar to those I use on FF 54, I'd probably switch to it.
Aside: a friend wants to get a new laptop/portable. Vista aside, I really liked my old Tosh (its video went south after 11 years). So we opened the Toshiba site and found they still have a 'Portégé' range. When I bought mine I think there were 3 models, now there are over 30 - which is absurd. Not only that, for me weight was a major consideration, as it is for my friend; my Portégé weighed in at 9?? grams; the lightest model in today's range is 1.5kg! But I did notice they come with Windows 10
Pro, which gets a big tick from me.
BR