HTC Vive having trouble with non-steam games

I've been able to run steam VR games just fine with my Vive. I have a couple non-steam, standalone games though that support VR natively (don't need something like vorpX). I've had substantial trouble getting them to work with the Vive. Usually when I launch them they don't even detect the headset (even though SteamVR is showing green across the board) and launch in non-VR mode if they support that, or outright crash if they're VR-exclusive. If I add them as a non-steam game to my steam library and flag them as a VR game, they'll launch in VR mode and show up fine on my desktop, but in my headset I get an infinite loading screen that looks like this:

If I move my headset around, sometimes it will flicker and show the game, but then instantly go back to the loading screen. I'm having similar issues with ROBLOX, another non-steam game, that is a little different than normal games. Games to play are selected through their website and then passed to the client so it can stream in the game (never installed/permanently downloaded onto PC). It doesn't detect my headset, and if I wanted to add it to my steam library I'd have to individually add different shortcuts to the client that point to individual games.

I've run Steam as an administrator, all VR hardware is using the latest firmware, and again SteamVR is showing green across the board. Out of pure luck sometimes I've gotten the games to work, but that seems really finicky because I'll be able to successfully launch a game and then not be able to launch that same game successfully an hour later.

Is this a known issue for the HTC Vive with a known fix?