welcome and congrats. the 28 Cut is a great boat
1. dinghy wise if you want to store on davits at the back it can only be 8'6" long to fit within the beam
there is a factory option which is pretty reasonable if a little heavy. some folks go with a portland pudgy. but its too heavy for my taste.
the cutwater is reasonably sensitive to stern weight and trim so putting something heavy out there is not ideal. the other anti heavy factor is trying to lift the dinghy when raising onto the davits.
I use a takacat and a 2.5hp suzuki for this reason. super light.
2. The dinghy can be longer if you want to tow it but almost no one does as its a pain
3. some people use 2/3 person kayaks and store them on the roof - lots of people have discussed pro's/cons before.
4. The cutwater bow roller restricts how large a anchor you can install. many upgrade to rocna or vulcan anchors. but only go up to a #10 size. as the #15 doesnt fit well. some folks have extended the roller, others have a slightly different spec size hole for some reason and can get a #15 to fit. the biggest different to anchoring is more scope and chain than one size of anchor up. perhaps leave this decision to after the purchase and you see the roller?