Your best bet is to get a clearance for your RPA initiative to have the Azure Windows Server running all day or atleast the RPA team should be able to schedule start/stop of azure resource.
The UiPath.Service.Host.exe service is the one performing the heartbeat checks and connections to the Orchestrator ( Service (uipath.com)). This service can be configured to automatically start after a restart (this is also a default configuration of this Windows Service). So after some seconds your Server is online, the robot connection is established with the orchestrator.
So in your case what is happening is your trigger, triggers the process but the VM / Server may be disconnected at that current time (UiPath.Service.Host.exe returns no response). Adding to security reasons, this is also done to save cost incurred to your Azure Subscription. This will lead to under utilization of your robot license, which can hinder your RPA ambitions.
Communicate to your IT / Business department that this security policy is hindering you from utilizing the robot licenses fully.
My expierence with Azure VM and UiPath has been quite smooth. I used schedules to cut down on unwated VM consumption. So this above method works, if you have the necessary rights to the VM / Server in Azure.