I struggle understanding how to scale objects properly. I know how to use the command and all but I don't really see how my co-workers figure out the scale factor. I think they look at the scale on the drawing like a 1/4"= 1' and go by that when I bring in blocks or text. I guess I am looking for someone to point me in the direction of a helpful video or explain it to me like Im 5 haha.
You should draw everything full scale in model space, regardless if you are designing a watch, or a 2 million sq. ft. factory.
Then you can "scale" the objects in your viewport when you create your layout. See this for more info.
Not sure if this is applicable to your case, but annotative text and blocks can help you resolve scaling issues. Of course, annotative objects open up their own cans of worms. The nice thing is that you define the size once and assign scales to the object as necessary.