Understand your anxiety
Yep, I single-hand my 37.5 a lot on the Ches Bay and anchor up/down can be a real challenge sometimes. Who needs coffee in the early am when you're trying to get it up and secured without hitting the mega yacht that achored WAY to close late last night? Gets your blood pumping early. A friend has a new big Bene with remote control windlass and self chocking (?) anchor. Very nice. He can raise it from the wheel, and it will set itself into the roller. Mine is not so user friendly and I have to flake the chain in the locker anyway, so there is no point in a remote for the windlass.We have a lot of mud, so once I bring it up with the windlass, either I get mud everywhere or try to hold the washdown hose, while I work the windlass, flake the chain, AND try to get back to the wheel before hitting anyone. I generally get the anchor up so that it clears the bottom good, but not up into the roller. I then take the wheel and motor out of the anchorage ~slowly~ effectively dragging the anchor through the water washing the chain and anchor off and getting me into more open water to finish off the raising, washing, etc.Peggy has made some interesting suggestions for raising it from the cockpit/wheel. When cruising, I keep a smaller anchor with rode on the stern, and sometimes set that for a lunch hook, or to make repairs, etc. But that approach doesn't work for a chain/windlass operation for an overnight/extended stay.And if it's really wind in the AM and you have to get going ... been there, done that too!