Best way to use a Win98 software in a Win7 machine

Hello, one of my clients wants to keep using a database software which doesn't work under anything beyond Win98SE.

If I try to use it in a newer OS, I always get an out of memory error, no matter which compatibility options I choose. Editing system.ini doesn't work either.

There is no convincing my client to upgrade the software, so my question is: which is the best way to have this software run under a Win98SE Virtual Machine?

The software handles two com port printers and a parallel port barcode reader, so I need the virtual machine to communicate with all these ports. Also, the software has a security usb key, and I need that to work with the virtual machine too.

Any suggestions? Thanks guys.
Daniele BrunengoIT Consultant, Web DesignerAsked:
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Gary CaseConnect With a Mentor RetiredCommented:
VMware generally does a better job with passing through hardware ports, so I'd install Windows 98SE in a VMware virtual machine, and assign it the necessary COM, LPT, and USB ports.    Note that even then you can sometimes have problems with security dongles -- but the only way to know for sure is to try it.

IF that works okay, then you're home free -- as you can then trivially move the "machine" to future hardware as needed (as long as it has the necessary ports ... which with modern systems will likely require a PCI card or two).

An easier approach is to simply install it on native hardware -- i.e. just "...  maintain an OLD PC that Win98 runs on ...", as mentioned above.    If you're going to do this, buy a spare (or two), while you can still get them on e-bay.    These computers are available for VERY little $$ these days.
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Lee W, MVPTechnology and Business Process AdvisorCommented:
I would say try it in Virtual PC (which is free on Win7 Pro and Ultimate).  It should pass through COM ports, Parallel ports, and most USB port devices.  BUT, I will say USB under virtualization, even VMWare, can be flaky at best.  At the end of the day the only option MAY be to tell the client you can do it.  It will cost tens or hundreds of thousands of dollars in development costs, but you can do it - because with enough money, anything can be done.

Or maintain an OLD PC that Win98 runs on.
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Dave BaldwinFixer of ProblemsCommented:
"Or maintain an OLD PC that Win98 runs on. "

That's what I do.  I have several old machines for specialized software including a Windows 3.11 machine that still makes me a lot of money.  And yes, I have a backup machine too, just in case.
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Use an Imaging Product, like Ghost or Clonezilla, and Clone to VMware Workstation or VMware Player.
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Daniele BrunengoIT Consultant, Web DesignerAuthor Commented:
Thanks, and sorry for the late response, I'm from Italy.

Before going the old pc route, I'd rather give it a try with virtual machines.

I think I'll test the security dongle with both Virtual PC and Vmware on one of my pcs. If it works fine, then I guess the other ports should be no problem on any pc.

I usually go with Virtualbox, but I've read it works quite badly with pre-XP Microsoft OSes.
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Gary CaseRetiredCommented:
Installing Win98 on Virtual PC requires a bit of a trick => you need to download the VPC-2004 version and extract the VM Additions from that.   Then you can install VPC 2007 and install Windows 98, but use the old version of VM Additions.

No such trick is required with VMware.   [And Microsoft MAY have fixed the final version of VPC 2007 so it doesn't require that trick -- but several years ago it was definitely necessary.]

Note also that VMware has a better chance of working with your hardware dongle, as it does a better job of passing through the physical ports.
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Gary CaseRetiredCommented:
Note that if none of those Type 2 hypervisors work well for passing through the hardware ports, there's another alternative:   Install ESXi (a Type 1 hypervisor) on a system and build a '98 VM there.   ESXi does a superb job of pass-through for virtually all hardware -- I/O ports;  video cards;  disk controllers;  etc.    However, you'd have to be sure you were using an ESXi capable system and CPU, which must support not only vt-x, but also vt-d hardware virtualization support.    This would almost certainly be more costly than the alternatives you're currently looking at;  but it's another choice if you need it.    [And the base ESXi is free]
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Daniele BrunengoIT Consultant, Web DesignerAuthor Commented:
Ok, I can test ESXi too if necessary on this machine I'm currently at, which if I'm not mistaken has vt-d.
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Check if the computer/server/workstation is on the HCL.

Check the VMware HCL (Hardware Compatibility Lists here

http://www.vmware.com/go/hcl
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Daniele BrunengoIT Consultant, Web DesignerAuthor Commented:
Judging by the price of required hardware, I'd say ESXi is out of the question...
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Daniele BrunengoIT Consultant, Web DesignerAuthor Commented:
Been a long time, but for various reasons the job was put on hold until last week.
And, it works wonderfully with VMWare.
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