Hi there, @Jnieman! Often times when a Doorbell Pro falls offline after a button push, it is actually due to power loss, even though you see messages about wifi. When power is lost, the wifi connection to the device is also lost, which might explain the wifi connection message you receive. To ensure this is not wifi related, please test other events such as motion or live view, to confirm that your network can handle streaming and communicating an event. I recommend also checking that your Doorbell Pro is connecting to your 2.4 Ghz wifi network, rather than a 5Ghz network.
If other events operate as intended and your network bandwidth is sufficiently operating the other features of this device, the best next thing to check are power variables. Please ensure your transformer is rated for at least 16v to 24v of AC power, and that your Pro Power Kit is installed per the manual. Thin or old wiring can cause resistance in power as well. Feel free to let us know how this goes!