Hi Scott.
Congratulations on your purchase, and welcome to the forum! Please feel free to ask any question.
As for windlass placement, that's something I've been struggling with for some time. I've seen several solutions, but all seem to have some shortcomings, or require fiberglass fabrication skills that I lack. The 323's fordeck layout does not readily accomodate a windlass.
One solution is to split the chain locker cover into two parts, with a built-up platform on the fwd part as the site for a horizontal windlass. The chain drop height into the locker is less than ideal, and will probably require some manual arranging of the chain to avoid pileups and jams.
Another solution is to place a horizontal windlass down inside the locker, with some sort of roller or skid plate where the chain will drag across the lip of the locker. THe fwd portion of the locker is above open space in the forepeak, so the chain fall can be thru a tube and into the forepeak, where it can be allowed to pile up in a basket or down in the bilge.
One of the members here built up the whole portion of the foredeck ahead of the chain locker and mounted the windlass there, with the chainfall thru the deck and into the forepeak.
Hull #18 (which I looked at but did not buy) has a fiberglass pedestal built up where the ventilator port was, and has a vertical windlass mounted there. The chain wraps around it 180 degrees and goes thru a hawse pipe in the sloped area just behind the stem fitting (see photos)
Honestly, though, in the 5 years we've owned the boat, while I kept searching for the perfect windlass solution, I've discovered that we've gotten pretty proficient at getting the anchor up by hand, even with a 33lb Bruce on 50 ft of very heavy 3/8" chain.