There's a JkDefragGUI that will handle setting up scheduled defrags, too. I'd get that and set it up to run at 3AM or some such. You might need to then edit the schedule (with the Windows "Scheduled Tasks" application) manually in order to have the computer wake up for the task, since it's a laptop.

Active@ Hard Disk Monitor is a SMART monitor for Windows. You can set it up to email someone when it detects problems.

You also might want to consider a VNC server instead of/in addition to Remote Desktop. RD won't allow you to control the existing display. There are a variety out there. I like UltraVNC because it can do domain authentication, but that's probably not a concern for you.