Heh, found it hilarious when i managed to install 95 on DosBox... Course without drivers to make it take advantage of hardware, slightly annoying vs say VirtualBox

Though aside from some compatibility, or accessing your compressed volumes from Doublespace/DriveSpace....

I got a few games to run on this EXE or zipped version of 95, runs better than DOSBox for some reason.

put 98 on that program and boom!

I really want to relive the days of 98, That was my jam

Hmmm.... well DosBox uses a non MS-DOS free OS, while Windows 95 was built on top of MS-DOS 7 (effectively). So having the base OS closer match would mean it probably would run better.

Or maybe it was tweaked to run better than DosBox... not sure.

Why wouldn't you do that? That is exactly what I would do. MS will keep the Windows 7 online updates available for years to come I think, so it is not like the ability to get the "latest" updates for Win7 will vanish when the extended support ends.

My current main gaming PC (an aging ASUS gaming laptop) is just like that. I have Windows 7 64bit on it (I have reinstalled it clean a couple of times, the last time was like a year ago), and installed Linux Mint XFCE beside it. When the Win7 support ends soon, by default I will keep the Win7 offline (by disabling its networking/wifi), and when I need to go online with that PC, I use Linux. I might still go occasionally online with Win7 if there is some specific need.

I would have an option for a free Win10 update for that PC, but I intend to keep Win7 on it for any games that have issues on Win10 and work better on Win7. I have a separate PC (laptop) with Win10 already, and my future main gaming PC will most likely have Win10 preloaded anyway. There is no simple answer to that. It totally depends on your other machine/network configuration, what will you do online etc. Like, are you behind a NAT router, are the Windows programs you use (like a web browser, antivirus etc. still actively updated on Windows 7, etc. Microsoft will probably stop giving Win7 updates for their antivirus and IE browser so if you are now using them, switch to using some third-party products like Avira Antivirus, Chrome/Firefox browser etc., as they tend to get longer support for unsupported OSes.

The more critical things you do (like online banking, any services and sites where you log in using username and password etc.), it might be a better idea to do them on the supported Linux side instead. Then again you said you wouldn't use browsers on it.

In general, the longer an OS hasn't received security updates, the more insecure it is. I also have two old retro-gaming PCs with Windows 98SE and XP, and I'd never try go online with them, no matter if someone claims they'd still be secure as long as I update their web browsers etc. (not sure if any web browsers or antivirus still receive updates on WinXP or 98SE). One of those PCs has also Linux, so if I need to download something online directly to that PC, I switch to Linux boot). In the coming years, my Windows 7 will be similarly 100% offline, increasingly so.

Not really sufficient, unless people are blocking all javascript and plugins and everything else under the sun. Most old hardware and OSs isn't getting full-fledged security fixes for various hardware vulnerabilities cropping up of late.

Take Intel's myriad of vulnerabilities discovered of late many can be leveraged via javascript in a browser. And even on "trusted" sites ad-networks and scripts can be hijacked.

Scaremongering on the part of the big corps interested in making people buy their latest stuff, which in case of software also takes over more control from the user.
As for those side channel vulnerabilities, like most "sky is falling" vulnerability scares in recent years, with one or two notable exceptions which could typically still be mitigated by a 3rd party firewall blocking all inbound connections and not opening fishy files or clicking fishy links, they weren't really exploited past proof of concept stage, or if they were those were usually targeted attacks on large companies or state infrastructure.

Lying to people and lulling them into a false sense of security isn't good either. No XP isn't safe, and no 7 isn't that great either nor is the older hardware... there's enough known vectors of attack that someone isn't going to block it by "sticking to safe websites" if it occurs.

Yes current and future OSs and hardware will have exploits and holes discovered too as time goes on. Freezing in place, but still faffing around online isn't remotely secure. Cause we both know only a handful of people are gonna be blocking all javascript, adverts, plugins, and etc.

And things like the WannaCry debacle... primarily impacted older OSs.

Is it because of the fallacious belief that an OS is much more virus/malware prone at or near the time it goes EOL/EOS? If so, then please note that such accounts are usually exaggerated &(as POST 2 says very well) still using an EOL/EOS OS is fine as long as you keep your AV/firewalls up to date and activated when online and use common sense when downloading/browsing/etc. It's not even necessary to change OSs if the above is followed properly. :)


=====================This....the main times other bad people usually(or so I hear) go after others individually is if they are high value individuals with sensitive data on their PCs.

(Also thanks for the other tips about firewall/etc....I seem to have forgotten some of them when setting up Win10 on my new PC)