I've anchored singlehanded about 80% of the time in the past 23 years or so. My boat is 42' LOA, weighs 28K lbs. Anchor is usually a 45lb CQR when out of the Chesapeake area, and a Fortress FX-37 when in home waters (Chesapeake).
No problem raising the anchor, though it sometimes takes some deft action when in close quarters.
I have an electric windlass (Lewmar Concept 2) with 200' of 3/8" G40 chain. The windlass has up/down buttons on the deck near the bow, and a remote up/down switch in the cockpit.
When the wind is really piping up, I generally use the engine to take in chain, using the switch in the cockpit judiciously. Sometimes, I power up toward the anchor, hit neutral, and move quickly to the bow where I take in more chain and watch what's happening. Sometimes takes a repeat trip or two until the bow is up-and-down over the anchor. Then, a gentle power forward or aft will break the anchor free, after which the electric windlass finishes the job.
I used to have a Simson-Lawrence manual windlass when in the Eastern Caribbean, but after one very dicey experience at Union Island with tons of boats around, a Christmas wind howling, and my younger-than-me crew just about having a heart attack getting the chain in with that windlass I decided it was time for a good electric windlass. Never been sorry, and never a moment's trouble with the windlass. Install 'em right and they'll do you proud for a long time.