Is it possible to connect multiple android smartwatches (4-5) to a single tablet/smartwatch and communicate on those watches with each other in a custom made app? The purpose is to communicate with employees with wearable devices in a customized android app for a business environment (the employees would receive tasks from a backend system and they can accept/decline those tasks and should be able to send information about their accepted tasks back). I would like to use a single tablet/smartwatch to lower the cost of a dedicated smartphone for each wearable). Is this possible with android wear or does anyone now an alternative to create a solution like this?
Yes, this is possible. All Wear devices paired to a given phone or tablet) exist on a single "network", and communications using the Wear APIs can travel freely among them.
A couple of specifics, with documentation links:
Updates passed to the Data API will appear more-or-less simultaneously on all connected devices.
Using the Message API, you can send data or actions from one device to another (like from the single phone to a specific watch, or vice versa), specified by its unique Node ID.