Scott,
In the setup I have one Red Convex LED Lighted Arcade Pushbutton from Paradise Arcade Shop and two NovaGemCDR Coin Drop Replacement Pushbuttons from GGG. They are run in that order from my Pac Drive.
I don't know how much current the Convex LED is rated for but it has a rating of 5V AC/DC while the Coin Drops are rated at 100 ma @5V DC.
I am plugged into my motherboard which is rated for 2.0 USB which I believe is strong enough to power the Pac Drive. I have a powered USB hub at the house which I have not tried yet.
The LEDs are run in a series. I have not tried to run them parallel. Last night I only plugged in the one switch that was giving me the problem and still had the same affect. Thinking it was a problem with the LED earlier I got a new switch but I am having the same problem.
I CANNOT say for certain that the Paradise Arcade button has the same value resistor as the other two. Is there any way to check with a meter?
The attached images are how Ultimarc shows 5V to be wired and how I wired it. I drew over the wires in Photoshop how it was wired. (Don't you like my killer 5 year old art skills?

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The button on the top left (because I couldn't get it in the shot) is the button from Paradise Arcade Shop. If any more info is needed let me know. I also included a picture of how dim the one button gets. The picture does not do it justice. There is a major contrast IRL.