OK, this is exhausting. Nothing seems to work with the anchoring system as designed/installed on our R27.
We decided to give it one last try: installed a new double-swivel to let the 'twist in chain or line unwind. Then did as "Chino" suggested: found a 110' deep hole in the Patuxent River and let out a LOT of rode.
Chain fouled in the gypsy repeatedly deploying, but finally got it all down. Another 50' of line deployed pretty much by free-fall after that. Waited 20 mins. in a fairly strong current for the anchor to twist and allow chain to unkink.
Then could NOT retrieve even the line! Anchor was dangling 100' down, so maybe with that extra hanging weight, it was too heavy for the Lewmar windlass motor? Repeated stopping (clutch full tight), "Down" & "Up" cycling over and over to clear the gypsy. Considered cutting the line and just going back to the dock!
Ended up, my friend actually volunteered to pull up ALL the line hand-over-hand while I took up the slack at the windlass. Not safe or easy to do. The system actually worked "as advertised" that way, but USELESS for practical anchoring purposes.
Finally, the chain began to come aboard -and surprisingly, all the links looked well aligned going into the gypsy and it retrieved reasonably well, with just a few stops.
My conclusion is that 50' of 5/16' is WAY too much for the boat..and certainly for Lewmar Model windlass installed. For this Model, 25' of 1/4" chain MAX. would be my guess. Next year there will either be a smaller, shorter chain -or a better windlass.