I haven't installed CFS2 on my Win 64bit machine for the very simple reason that I have lost one of my install Discs ! The problems seem very similar to getting the MS Train Sim to run, and they mostly revolve around permissions.
1st - do not install it in the default 'Program files (x86) location but create a separate folder on your C:\ drive ( or better still, on a different drive, if you have one ).
2nd - do not run the installer from 'Auto-play'. If that comes up, close it, then use Windows Explorer to find the install set-up file on the CD. Right-click on the installer file and select 'Run as Administrator' from the pop-up menu that appears.
3rd - when the installer starts to run, select 'Custom install' and point the installation at your dedicated folder, then let it do its thing.
4th - when it has finished installing, don't run it straight away. Go back into Windows Explorer and right click on your CFS2 folder. Select properties from the pop-up menu. Then set all the attributes to 'NOT read-only'.
5th - Click on the 'Security' tab at the top of the property box and ensure - by using the 'Edit' tab if necessary - that ALL users have full permissions, ie ALL the boxes for ALL users are ticked. You will need to be logged in as an administrator to carry this step out.
6th - Re-boot, and you should be good to go.
CFS2 is from roughly the same date as the MS Train sim and has much the same difficulties. I know the above works - my copy of MSTS is now running fine, all I need now is to find CD 1 from CFS 2. It's here somewhere, I hope !