I know one tab is larger, so I'm getting it started correctly, it gets about half its needed turn and starts to bind. Taking the seat off helps, and using a rubber strap wrench helps, but it's gonna break.
Does it really need to be this complicated?
Is there a simpler aftermarket option?

 

You didn't mention what year of Sportster, I'm guessing 2004 or newer. The oil stick only turns in about half way then you push it in till it clicks. Mine's a little snug but never had it where I couldn't turn it.

 

Sorry, I just thought it was common knowledge across the globe that the wife bought an 05.