Anchor chain pyramiding and jamming

One easy item for folks with chain is the concept of installing a line at the bitter end which can be cut to free the boat if required.

Better to install 2 lines , one free so you can tie a float on , while under heavy load , to locate that expensive ton of chain, before cutting it loose.

Using a grappling hook later to locate it on the bottom is an iffy deal.

On the Monk36 I made it a routine to rearrange the pyramid manually thru the vee berth chain locker door to avoid jamming each time I hauled in the chain.
I like the specs on 5/16" HT chain, it worked well on the Monk36 so when I was removing a very marginal rope windlass on the Manatee I ordered the same chain size for the Ideal windlass I installed.
Your correct FF, I rigged the bitter end of the chain with a three strand pennant long enough to bring up on deck and attach a float or detach the chain and drop it in an emergency. I would use the MOB on my gps to mark the location.
Bill

Use the hockey stick, or a version of this.

I use the windlass handle, with which I reach down into the chain locker while the chain is being wound in, and I knock the top of the pyramid over as it builds. This means I am on my knees while bringing in the anchor, but I no longer have the pile fall on itself the first time I hit a large wash.