Hi seanr24, and welcome to SAF!!
If you're not able to restore the files from the Recycle Bin while in Safe Mode, you'll have to go into DOS mode in order to attempt to restore the registry.
The "last known good" backups for User.dat and System.dat are the User.da0 and System.da0 files. If you deleted either or both of them, then you don't have a recent registry backup that you can use to restore the User.dat and System.dat files.
Here is what you'd do to restore User.dat and System.dat from the .da0 files:
When your computer is starting/restarting, keep tapping the F8 key in order to invoke the Startup Menu. At the Startup Menu, select Safe Mode Command Prompt Only.
Change to the directory where Windows is installed (usually the C:\Windows directory) by keying in, at the comand prompt:
cd Windows <ENTER>
Now key in the following commands, one at a time, hitting ENTER after each command:
ATTRIB SYSTEM.DAT -h -r -s
ATTRIB USER.DAT -h -r -s
REN SYSTEM.DAT *.OLD
REN USER.DAT *.OLD
ATTRIB *.DA0 -h -r -s
COPY SYSTEM.DA0 *.DAT
COPY USER.DA0 *.DAT
ATTRIB *.DAT +h +r +s
Hit Ctrl-Alt-Del to restart the computer
If the above doesn't work out for you, you can restore the registry back to when WIN95 first successfully started:
ATTRIB SYSTEM.DAT -h -r -s
REN SYSTEM.DAT SYSTEM.OLD
CD\
ATTRIB SYSTEM.1st -h -r -s
COPY SYSTEM.1st C:\WINDOWS\SYSTEM.DAT
ATTRIB SYSTEM.1st +r +s +h
Hit Ctrl-Alt-Del to restart the computer
You will have to reinstall any applications, etc., that place entries in the registry.
If neither of the above work out, you'll have to reinstall Windows and all applications that place entries in the registry.