Usually, after the chromebit reboots, it should connect to the internet straight away. If it doesn't it could be that the wifi signal is weak or is being blocked by the TV.
First, determine how far your device is located to the router. Is the Chromebit connected to the TV screen via the HDMI extender or is it hidden behind the screen? If so, that would one of the reasons for a poor WiFi signal. TVs have a lot of RF shielding in them and will likely block WiFi signals going to the attached device.
Please try to use the HDMI extension cable to position the Chromebit away from the back of the TV? See if you can improve the signal that way.