Every so often I get a call from someone wanting help moving a boat. It is usually 50 to 150 miles, east coast, typically Long Island Sound, RI, CT, NY, NJ.
Pretty short hops. Ground transportation is likely to be a bigger issue in many cases than moving the boat.
My thoughts as a delivery skipper follow. Most of my work is long haul offshore but I do my share of local moves also, mostly single-handed.
Nav lights are not negotiable. You never know what might happen except that the sun will go down.
You can never have too many fuel filters.
Ground tackle is important. Appropriate anchor, rode, snubber for chain.
Are there enough fenders and dock lines for arrival?
Educate yourself on towing insurance. If you are being paid to move the boat your own Towboat/US policy does NOT apply, and the owner's doesn't either if he isn't aboard. I don't know the details of SeaTow policy. Towboat/US offers a separate delivery skipper policy I highly recommend.
Meals and snacks need real attention. You have to keep energy levels up. You have to be alert. On short trips you can get away with cold pizza and PBJ but there has to be enough and you have to make sure everyone, including you, eats. Good food helps make good trips. Hydration is similarly important. For short trips as you describe, a couple of gallon jugs of water is plenty in case there is a problem with the water system. If the boat water smells or tastes funny you'll want more jugs.
Other things from my own list:
Spare batteries for all portable electronics
Adapters to charge phones et al from 12V
I think damage control prep is often overblown. If you have duct tape and wood screws you can manage nicely in extremis with locker doors and floatation cushions. The latter you're going to want anyway to sit on.
Remember that real problems are rarely single events. It's a cascade of two or three failures that lead to a crisis. Deal with every single thing that fails as quickly and permanently as possible, even if that means breaking off a passage.
As you're sailing think about things that might go wrong and what you would do in response. It's good practice, and when something does go wrong you'll respond more quickly.
I do a lot of owner-aboard deliveries. You have to have a discussion about who is in charge before there is a problem. Are you skipper or crew? Do they just need support or are they looking for training? Are you in a position to meet the owner's expectations? Communication is key.