Windows 95 can be obtained as an ISO from websites like winworldpc.com, but it may face compatibility issues with modern hardware and software. Running Windows 95 on a virtual machine is a viable option, though users might encounter challenges with video and sound card drivers. It is noted that Windows 95 poses significant security risks, and alternatives like Windows 7 are recommended for better performance and security. Multi-boot setups with older operating systems like Windows ME and XP are possible on older hardware, but care must be taken with drive letter assignments during installation. VMware Fusion supports older Windows versions, including Windows 3.1, providing additional options for users interested in legacy systems.