If VMware Player worked out of the box as it were for pre-XP Windows virtual OS's it would sell.
VMware Player is free.
Workstation 8 supports guest OS's of Windows 95 and 98.
Workstation 9 has them deprecated.
The issue is going to be at what point do you stop supporting the old OS's.
From a logical perspective, if VMware had support in Workstation 8 then what would be the reason for deprecation in Workstation 9. Only they can answer that.
However, Microsoft hasn't supported those OS's in years, so after the initial OS install there is no updates support, etc.
Anyone who has software that dates from 15 years ago that won't run on at least Windows XP either has to use previous versions of VMware Workstation (version 8 or earlier) or Virtual PC (no Windows 8 host support) or another supporting VM package, or they need to freeze a computer system at that level and pray that they never have a hardware failure sinec no new hardware has driver support that far back. The best alternative is simply to move to newer software and remove the dependancy on such old OS's.