@realbrianlouden
I think uploading videos is discouraged due to bandwidth/storage costs, and they'd rather you upload somewhere else, and then link here. But I'm new to Mastodon as well so maybe I'm misunderstanding

One thing I can recommend though is to not use the official app on iOS and Android. It's recent and still playing catchup. I recommend either just adding your server's website to your home screen, or getting a third-party app. For iOS I've seen people recommend "Metatext" or "Toot!"