Hi Scott,
If you want to go down the monitoring of VPS path, then have a look at ServersAlive:
http://www.woodstone.nu/salive/editions.php
http://www.woodstone.nu/salive/features.php#
They have an unlimited time free trial period. The ‘free’ version restricts you to the number of devices (10 devices/entries) you can monitor, but that might be enough for what you want to achieve.
It performs email/SMS alerting, can restart services, run batch scripts/executable files after an alert etc.
So it might suit your needs.
Regards
Glen