Anything over about 55-60 mph and you get a rolling oil change. Have you been riding fast lately?

They don't go through oil really fast but you do need to keep a check on the level before you ride.

So what if your a newbie, and you forget to check your oil once in a while and it goes below the window ( not saying I don't check my oil) where is the super danger zone? I've gone a little low once or twice.

Kris01 is right, on the one really long trip I ever did, Our leader arrived at the start and after 100 miles or so, complained his Harley Thingyason was wandering about. Turned out he had 12 psi in his back tyre.

So when do I check the oil to make sure it's at the right level, I've heard people say hot, and others say cold. I'm assuming cold, am I right?

Some have even set it high enough to see while on the sidestand. Low isn't good. It can use oil at any old time.
Watch it carefully, especially when you run it hard.
Monitor the use and you'll learn when it uses oil , especially as the miles add up on the oil. I don't think I made 3,000 miles, ever. Towards the 3,000 miles mark mine was using fast enough I just changed it.

Well the manual does say to run it for 3 minutes then let it sit for 5.

So you do that every morning?  Right    If that's normal for you, don't let me stop you.
It might necessary on frosty mornings in Denver.

I don't have time for that BS.  I put a brick under the stand, check the level and I'm done.
3 minutes doesn't warm the oil much anyway.