We lived in the same world. You're an old fart, too, I see. Those were the days. Windows was useless until Windows 386. DESQView was the way to go. I used it briefly for a multi-line BBS until I switched to TBBS which was natively multi-line. Windows 95 was a joke compared to OS/2. I never went beyond OS/2 Warp 3. I switched to Windows NT and have been with them pretty much every alternate version since. I'm running Win10. Screw Windows 11. When Windows 12 comes out, I'll wait a year and then think about getting it.
Cats4U
Ahhh DesqView. QEmm386.sys. Its why I upgraded from a 286 to a 386sx so I could use QEMM to use the memory above 640k, and multi task, rather than task switch. Did you ever try DesqViewX? I played with it a little, but never really got comfortable with it.
BBS? Most of the ones I called used Wildcat. Fun times. Man i racked up phone bills for those long distances calls to BBS's back in the day!
I did use Compuserve, Genie and Prodigy.
And I did get started on a TRS-80 Mod 1...  My first home computer was a Kaypro II that ran CP/M!!   Ahh hex editing Wordstar config files to add the escape P commands for my Star Micronics and Epson dot matrix printers so I could print in bold, italics, double high, double wide, super script, subscript, etc.  
Swapping EPROM chips to do a "bios upgrade"... yeah, no flash bios on my Adaptec 1520 ISA SCSI adapters :D 
Those were the days...