1. I noticed there is some play in the comp-tip/mast joint location, is it supposed to be more secure or is it normal to have some movement?
The CompTip should be epoxied in place.
2. Installing the Cheata Motor Mount and 2hp outboard, are there any new requirements with boating laws or the insurance policy?
Adding a motor to a sailboat changes right of way rules when being used. Check with the USCG. I would ask your insurance agent about differences in coverage required.
3. Shroud cable insulation covering rubbed down to the bare cable, should I buy a new shroud cable or is there some way to repair the covering?
If the wire is intact (not damaged) you can use tape or similar to protect the wires. Look at what caused the wear and remove any sharp edges.