I'm downloading directly from the catalog on the actually playdate console and it will either result in error because of internet issues, or it just flat out says "ERROR Try downloading this game again?"
I've tried downloading it numerous times thought the day and the same messages kept popping up.
Can someone help me resolve this issue?
This is a Developer forum, but I'll try to help.
One thing you can try is getting closer to your WiFi access point, or trying a different one. Your phone might be able to act as one. Some WiFi points act strangely (not just for Playdate, just in general).
Also keep in mind the Play.date runs on 2.4 GHz Wifi, which is more prone to interference from Bluetooth and others. While my phone and laptop have good wifis throughout my whole appartment, to download games I basically have to be in a short radius around the router (also because it's in a metal thing, but that's another story).