Stern anchor suggestions
It sounds like you have more of a need for a kedge anchor and a 2nd bow anchor, neither of which would need to serve as a ''real'' stern anchor. E.g. I think you''d be happier doing your Bahamaian moor with two bow anchors, for multiple reasons.
For portability - when needing a real kedge anchor & rode - I think your not sticking to your namesake (W&L) by trying to use your 35# Danforth. It''s certainly not easy to handle, by weight, form factor or dimensions, even before the weight of the chain is added. I think this is why having a Fortress on a boat is quite helpful. It''s light weight (and in the right conditions, super holding power) make it an ideal kedge.
I''m thinking that one of the ''must do''s'' for WHOOSH is to add some kind of sacrificial surface against which the chain can grind and scrape, on the outer side of the stern roller, to protect the gelcoat and the caprail back aft. I''m carrying some PVC sheet back with me for that reason.