<...> Win-98 SE was definitely one of the higher points of the Windows lineage. For most of what I did (and do, for that matter), it worked very well; it would have been nice if it recognized USB storage devices natively. The hardware is worth worrying about. Replacement power supplies will probably continue to be available, but those disks are likely to be unobtanium, and are practically guaranteed to fail at some point. My personal "sweet spot" for operating systems was Windows XP, and it was with with quite a bit of trepidation that I eventually moved on to Win7-32. Eventually, I needed a new laptop, and moved to Win8.1-64, which took a great deal of massaging to make comfortable (the "Classic Shell" product is very nicely-done, and free, and went a long way towards making things usable). However, there were still a lot of problems: - 64 bits absolutely breaks any 16-bit code, whether it be a DOS program or a Windows 3.1 application. Unfortunately, I have a large industrial application that I've maintained for the last 20 years (things last a long time in industry), written in Visual Basic 3. Maintaining it under XP was easy, because XP would just magically fire up ntvdm (NT Virtual DOS Machine), then run a Windows compatibility layer (wowexec) on top of that; this all made everything work just fine, and with almost complete transparency. For DOS programs, it would capture any physical I/O calls (for example, to the com port addresses) and do a fantastic job of emulating them - again, completely transparent to the application program. Win7 (Vista, actually, but nobody cares about that) broke all of that. - I have an application that I like and use a lot (CircuitMaker-2000) which runs fine on every version of Windows from 98SE on up to at least Win8.1-64 bit, and presumably Win10, though I haven't tried it. However, printing has been broken on everything since Win98SE. - The versions of Office and QuickBooks I was using started exhibiting numerous problems; Word continued to work "OK", sort of, but QB was completely unstable, and I depend upon it to run my business. - The security implementation of pretty much everything, starting with Win7, makes a lot of things difficult; registry writes are now tightly controlled, registering DLLs and OCXs requires elevated privileges, network firewall functions are highly complex, convoluted, and depending upon the version (Premium, Pro, Ultimate, etc.) the tools may not even be provided to completely manage all of this. My solution to most of this (except some of the network issues) has been to use VirtualBox. It's free, and does a great job of handling XP as a guest operating system. With XP, mouse movements, virtual disks, networking, and even the clipboard are all nicely integrated into the host operating system, so my XP machine is always just a keyboard shortcut away. I also have a virtual Win98SE machine, to handle the printing issues with CircuitMaker. This is less well integrated, in that the mouse capture is clumsy, and the file system integration features aren't there, but that was easy enough to get around by just creating shared folders on the host, and setting them up as network drives on the Win98 VM. It took a solid week of tinkering to get everything set up to my satisfaction (I have a lot of disparate interests, and their associated applications), but now I have a setup that I'm very happy with. (I broke down and advanced a single version - to 2003 - for both Office and Quickbooks, so those both run happily in native mode now.) Almost certainly not, at least practically. Even if you can get it to boot and install, it will have no idea how to handle any of the modern peripherals, and drivers certainly won't be available. So sound won't work, the screen will be limited to VGA-16, and I'm not sure about the keyboard and mouse (there's a reasonable chance that the BIOS will emulate the legacy PS-2 devices, just as it's abstracting the details of the SATA disks). I really think that your best solution would be to go the virtual route. Get a huge monitor (mine's 28" 2560 x 1440 - I would have preferred an even larger curved 4k unit, but HDMI wouldn't support it at full resolution, and that's all my laptop has) - or even a dual monitor setup, a terabyte or two of hard disk, and plan to spend that week tinkering. As much as you like Win98SE (and I completely understand why!), you might find that XP will still run everything you're interested in, and VirtualBox handles that very well. There's every reason to expect that the virtual machine will continue to be stable and supported for the foreseeable future (like 20+ years), regardless what the host Microsoft operating system evolves to be. Of course there's no reason not to have both XP and Win98SE VMs, as I do - I even have a Win3.1 machine, just for the fun of it. For backup, I stubbornly store everything in two large directory trees: C:\Library and C:\Data (actually, I have a C:\Music as well). The C:\Data tree has absolutely everything that I've ever worked on: source, designs, correspondence, pictures, taxes, email store, and the VM disks. It takes a bit of persuading for the modern versions of Windows to accept C:\Data as the "My Documents" folder, but it can be done. The C:\Library tree has all kinds of documentation (PDFs of manuals and data sheets, and lots of just plain reading material), as well as a large sub-tree called Distrib that has the installation sources for all my software applications. In some cases, this is in the form of ISO CD-ROM images, but mostly it's sub-directories with the contents of all those. Everything is there: all the Visual Basic/Studio versions, all the Office versions, compilers, Adobe, Photoshop, PLC and other development systems, SolidWorks and AutoCAD, and even the installation media (in both ISO and file formats) of the Microsoft OSes as well (DOS through Win-7). All of this fits comfortably on the single terabyte drive that came with the laptop, and backing up is a simple matter of either just copying the two (three) large trees, or using some difference software (I use a free program called TreeComp, but there are many others too) to sync everything to an external USB (3.0 strongly preferred) drive, which I keep in the fire safe. Moving to a new computer is simply (if time-consumingly) a matter of copying those trees to the new machine, then installing the software directly from the \Library tree - no other CDs required. It's probably possible (although the weak link would probably be the disks), but if it were me, I'd treat that more as a hobby project than as a machine I depended upon. So far, I've successfully avoided giving up the applications and "way of doing things" that I like and am comfortable with, while still migrating to current hardware and software. I have to admit, effectively unlimited speed and space are quite nice... ~~ Mark Moulding