you should not need to reboot the device to install the monitoring scripts into the device, does your firmware have the packages already pre-installed or do you install them by hand or with a script?
by default, OpenWRT does not contain a crontab file, which will cause the cron process to not start.
When the cron is installed by OpenWISP, the cron process may not be running and the reload script will not start it (because reload operations only reload running processes, they don't start non running processes).
One solution is to include an empty crontab file in the firmware image, which makes cron start and do nothing, but it will work out of the box when installing the template.
Another solution is to ensure the crontab is started at boot with a couple of commands:
touch /etc/crontabs/root
/etc/init.d/cron start
Regarding sending commands to devices, OpenWISP does not have this feature yet, but it's on my todo list for the next release, I just noticed it was not in the issue list so I created the issue of the things I will be implementing:
https://github.com/openwisp/openwisp-controller/issues/253It's a feature many people have asked, although in my experience, once the system is set up correctly, it will not be really needed, but I understand it's handy for many situations so I'll be working on it.
I hope this helps to fix the issue you're having! Let me know.
Federico