Take a negative that prints very easily and well into the darkroom. Dunk it into some water and compare the developing negs with this one to see when the highlights are about the same. That's my suggestion...
Personally I didn't have any negs to compare so I did a test with 6 negatives to see which film speed and developing time printed the best for a "normal" contrast scene and the next time I went into the dark I just judged based on what the previous negs looked like.
The IR goggles also make loading film holders a snap!
I really wouldn't call it trouble at all. It's like developing film with the room light on once you get used to it. The reason I started doing so is that I have weak night vision and was having trouble inspecting with the dim light.
When I DBI I look at the base side by reflected light from the green safelight. The base side is a milky white color. Check the base side about half way through & you'll see the milky white color without any sign of highlights. Check again at predetermined intervals & you'll see the progression of the highlights getting darker through the milky white base. When my negs are done for Azo printing, the highlights are coming through fairly strong, but not too much. I had to develop & print a few to get comfortable with judging the highlight density I wanted for Azo. It's a lot of fun. The IR goggles really sound like fun.
There's a difference depending on the developer. Non-solvent developers were called surface developers for a good reason: The emulsion side turns black long before you see anything through the base. So you should know what to expect with the developer you use...