@dLj,
You keep saying this. I don't know why. If there is someone dragging down on me, I want out of Dodge right away, not to stay there only a bit further away, and before I did anything with my anchor, I'd motor off to one side if I could.
Let's take your primary with what you've said IIRC a twice oversized anchor (also a dubious choice, but a separate issue and discussion, though), and your 300 feet of chain in 20 feet of water, so you only have 100 feet of chain out.
How long will it take to let out your next 200 feet of chain? What's at the inboard end of that 300 feet of chain? A rope rode? How long? What connects it to the boat? Another line to a cleat or tied to something? Wouldn't it take twice as long to let 200 feet of chain out than pull up half of that length (100 feet)?
What if there are shallows or land behind you? What if there is another boat behind you?
Most authoritative resources indicate that if an anchorage is untenable, one of the best things to do is leave or relocate.
I think you need to reconsider this "Let more scope out and/or dump the whole rode system" a tad more.
Motoring off to the side and pulling UP your rode may well be performed in a much, much shorter time.