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windows 98 repair install?

It's been a while, but I've got one user that still uses Win 98, for some (obviously!) very old program. Recently it wouldn't boot, saying it can't find win.com. I replaced (or restored) the file & now it's saying it can't find himem.sys is missing. Will a repair install fix all that?
It's been a while...
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Other than reinstalling it over top of itself, but you may be better off to make a new virtual machine of Windows 98 (because the hardware will fail). Virtual machines can last forever. VMware Player is free and can make a new Windows 98 machine
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HD Diagnostics checks out fine.
MASQ, yes, I have been there. When trying to extract file, I kept getting message that the cab file couldn't be open, read, or something. I put Win98 CD in another computer, extracted cab file to there, copied win.cnf, renamed to win.com, copied them to a CD, copied back to problem machine & that when himem message came about. All this is used for is medical billing work, done in Word Perfect 5.1 & thyere are basically 2 folders that everything resides in. Currently copying these to a USB drive, in the event repair install doesn't work & I'll have them for a re-install. As far as any virtual machine, wouldn't I need to have my current Win98 up & running fine to start that process? I'm also assuming that WP5.1 will only run under windows? Once I get back to square 1, I will be making an image of HD for future use & tell user to periodically back up prd & Wp51 folders!
As far as any virtual machine, wouldn't I need to have my current Win98 up & running fine to start that process?

More robust and reliable just to make a new virtual machine. That is what I would do (and did).
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Never had any experience with VMWare Player - I'm assuming this would be like running XP mode from a Win7 computer?
Where's a good starting point to delve into this, because I was wondering what to do with all the free time I had this morning, ha-ha!
On the bright side, they could get away from this antiquated Win98 box...
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Also test the RAM on that PC using memtest86+, also on the CD I mentioned above.

There shouldn't be any problem importing files made by wordperfect into other word processors. Just try opening them in LibreOffice or OpenOffice for example. It may just work, then save the files in a more used format.
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Would you notice much improvement in the way it runs? Assuming user went out & picked up the latest & greatest computer running Win8, while the hardware would be vastly improved, they would still be running Win98. Since current HD is only 80GB, I'm assuming I could just back up the VHD & it would be easily restorable?
I may give this a test run on my own computer...
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Will check the ram, rindi, but as far as moving them to a new word processor, this is one of those people (she's an older lady, mid 60s, if I had to guess?), who doesn't like change, ha-ha!
Would you notice much improvement in the way it runs?  <-- I have a Windows 8.1 Pro 64-bit laptop with 8 GB of memory and a fast (7200-rpm) hard drive. Windows 98 runs very well on that.

With VMware Workstation (not free), I can run the machine in Unity Mode - that is, I have a menu for Windows 98 applications that appears just above the Start button. This makes it very convenient.
Mid 60's isn't that old, and you may have to support this for another 2 decades or so. Besides, if she has to learn Windows 7/8.x or 10 on which you'd virtualize Windows 98, you might as well teach her to use a new word processor.

If it is the DOS version of WP51, it should also run fine from within DOSBox, on any Windows PC, no need for virtualizing w98.
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Suggest you get the Win98 box resurrected first but yes, then look at virtualization.  If they are just needing the familiar blue screen of WP5.1 you can emulate this inside current 64bit systems with DOSBox.

Have a Google for and play with WPDOS.

The advantage of a complete VM though is you've got a copy of the VHD as a backup and can have it restored in a matter of a few minutes :)

(And 60 is the new middle-aged :D)
Windows 98 runs very nice on a modern machine under VMware ... boots in ~ 30 seconds (clearly this depends on the specific hardware you're using) and runs WordPerfect v5.1 just fine ... I've got a '98SE VM with precisely that setup that I created several years ago.      The issue with doing a new install is that Microsoft's Windows Update site no longer works with '98.    Not a problem for those of us who saved fully up-to-date '98 installs a few years ago; but would preclude getting a new install fully updated.

There are a couple sites that created unofficial "Service Packs" that install ALL of the Windows 98SE updates, so if you install '98 from an original 98SE installation CD and then apply these you'll have a fully up-to-date VM.    If you have both a 98SE install CD and WordPerfect v5.1 installation media, creating a new VM with this configuration would be an excellent way forward.    This would let the user use a new machine -- and you can backup the entire configuration by simply copying the VM files.  (which you can also move to any machine you might need to)

By the way (FWIW), WordPerfect v5.1 runs just fine in XP ... so you could also do this with an XP VM, or in XP Mode under Windows 7.
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Yes, I did not mean to offend anyone, as I'm about to hit 56 myself!
I did get 98 resurrected & everything appears to be fine.
I've known this woman for probably 15 years & she is not one of those who wants to learn new things, although the prospect of running WP on a new computer with DOSBox sounds like a possibility.
'98SE actually runs very nicely in a VM, so if she truly doesn't need any functionality from it except Word Perfect, and is comfortable with it; there's no reason to not simply set everything up in a VM.

In fact, since you've got the system working well, VMware has a "P2V" tool that will do a physical to virtual translation, allowing you to create a virtual machine from the running version of '98.   https://www.vmware.com/products/converter

Might be worth giving this a try, so you don't have to worry about any future hardware issues with the old system.