I had the same thoughts about a windless.
Decided it was not worth the time or money.
My solution:
Pick the right anchor for the job
Don't anchor deep, and if I need more mojo, I run the rode up to the 2 speed winch on the mast.
FYI: 35lb CQR w/ 300"rode 5/8s 60" 5/16 chain
22lb Bruce w/300" 5/8" rode 60" 5/16 chain
22 Danforth w/ 150" 1/2 rode 30" 5/16 chain