I added a lewmar v700 to my Wellcraft v-20. it would self deploy a delta anchor off a standard simple bow roller. was nice when stopping off in a bay to anchor for the night or for a day of refreshments/bbqing. was so much nicer then hauling anchor by hand.
you'll likely need 2ga from your battery, to a circuit breaker up to the contractor, then to the windlass.
a factory pulpit would be nice. - make sure you have enough room for the shank of the anchor to nest in the roller before it hits the gypsey
mount the windlass as far back as possible to maximize free fall into the chain locker. this will make the windlass work better and maximize your capacity.
select your rope/ chain lengths. 8 strand is much nicer then the 3 strand rode. 15-50 ft of 1/4" chain and 150-200ft or 1/2" rope. (make sure everything matches the gypsey)
many of the choices you'll make will be dictated by local conditions or what you want to do with it. like if the bottom is often rocky id want 50ft of chain instead of 15. A longer chain also has more give to it if it gets rough/windy. if your sleeping over night id upsize to a heavier anchor vs if I was just day tripping. As for what anchor...its kinda like ford vs dodge vs chevy, but id recommend a rocna, a delta, or a bruce. but avoid all the knock offs (ie a sea choice branded claw)
if you can do basic wiring, comfortable drilling holes in your boat then its an easy upgrade. go for it, you'll love deploying the anchor with a switch, and retrieving it with just a push of a finger