How can I be sure a windows volume will boot up before restarting the server

You can't be sure without trying. But if you check the state of your disks in your RAID management tool and they are OK, and if your eventlogs don't show anything out of the ordinary, it is likely it will boot fine. If your server has an iDRAC or ILO (or similar, depending on what the manufacturer used) that should also show you the state of the hardware.

Thanks, but actually I'm looking more towards the boot partition, not so much with hardware problems. I thought about using something like "Chkdsk" to scan a volume for boot errors before I restart the server. I had a data volume that would not go online after the server was reboot, even though the volume was online and accessible before the server was rebooted.

I also had a file-system that would not mount or go online. After running chkdsk (drive letter) /F it fixed the errors and allowed the volume to be mounted. I don't remember which error messages chkdsk displayed during the repair. Would you happen to know which chkdsk error messages would point to a problem that would stop a volume from mounting?

No, but generally those would be errors it wouldn't be able to repair. If something like that happens it is very likely that your real issue comes from bad hardware, like failing disks or bad RAM, as that would usually cause file-system corruptions.