What you are looking at is to run a scheduling program to run as a Windows Service. Thsi service has to monitor time and run a particular EXE file at scheduled times. Schedule to be setup through a GUI. Remote monitoring 'Ping' also has some difficulties. If pinging from LAN, it is fine. Else we will have to use some other strategy.
We need to discuss about
how the program to be run will be specified,
how the scheduling will be specified,
What about specification about day of running,
date of running,,
how to specify exceptions,
How to Ping,
Is piniging required from outside LAN
Can the machine have a static IP address
A server module is required to respond to Pings
can a periodic email strategy be adopted
The job is not all that SIMPLE !
Relevant Skills and Experience
Have done quite a few applications on Windows . for control and monitoring applications
Proposed Milestones
$222 AUD - Project delivery. Final price will depend on final specifications
We need a good discussion to decide teh strategy to be adopted for this. There are several ideas