Wow, so many questions..
First you don't need 300MB for a /boot, 20MB is plenty. It's only there to hold the kernel and initrd. In fact it's entirely possible that you don't even need a /boot partition depending on your hard drive and BIOS, but you can't go wrong if you create one regardless of whether it's necessary.
Second, you can use VNC to remote control Windows machines. You'll need to install the VNC server on the windows machine and then use vncviewer under Linux to remote control.
Third. Assuming you mean reinstalling LILO from the Linux command line, and assuming you have your proper "/" partition mounted from your hard drive, just run "/sbin/lilo" (assuming you have not made any changes to your /etc/lilo.conf file. If you want to change the LILO boot menu you would change it in /etc/lilo.conf. After every change you have to run /sbin/lilo to make the changes active.
If you screwed up your boot menu, you can always use a boot disk or your CD to bootstrap your "/" partition on your hard drive. To do this, boot from the alternate media (CD/Floppy) and at the LILO: prompt type "linux root=/dev/hda2" (assuming your linux "/" partition is on your second partition of your hard drive). Once booted you can fix your lilo.
[ March 16, 2002: Message edited by: VoidMain ]