Headlamps are a poor choice for low light environments. You spend a huge amount of time shining lights in someones eyes (when they call you and you turn to look at them). I have a "one strike and you're out" policy - nuke my night adaptation and I confiscate.
Headlamps have their place for maintenance and repair (generators, radios) but come with the responsibility not to turn your head away from the task at hand. Ever.
I use these https://www.amazon.com/Flashlight-Pocket-Sized-Adjustable-Waterproof-Flashlights/dp/B071WK4R76 and their USB rechargeable equivalents.
Yeti makes good stuff and my 85qt cooler is wonderful. It straps in the back seat of our car, in the back of my truck, and on the aft deck of my boat. For portable storage and especially travel I prefer SealLine. My 118l backpack has more air miles than most people and has gone swimming with two laptops, a bunch of other electronics, and a mornings worth of clean laundry.
When I had my boat built in 2006 I put in more fans than the factory thought was reasonable, house power and 12VDC everywhere there might be a pillow, and a ton at the nav station. Since then there is USB A (first) and USB C in all those places. None of that is standard on any production boat and boats bought for charter rarely have such options selected. Too many people in the decision-making process who don't actually sail over time or distance.
I carry spices in Zip-Lock bags. I'm not so worried about glass breakage (an over-rated problem in my opinion for people with just a little care and awareness) but for packing space.
Don't let your MIL near your knives. At home, we have my knives and my wife's knives, a couple of visitor knives, and my travel knives.
My experience is that phones/tablets as hotspots work but not nearly as well as a dedicated device. I'm now carrying a Netgear Nighthawk M6. Better radios and speed delivered on the WiFi side is much better than from personal electronics. Most people don't travel as much as I do so it probably doesn't make sense - certainly not just for a charter trip.
There is no difference in the ability to pick out a boat name between using a head lamp and a handheld lamp. The problem with head lamps is that when someone talks to you and you turn to respond you destroy their night vision. I use Infray penlights and carry two or three that use AAA batteries and one rechargeable on trips. Day to day there is always one in my pocket. Pick what you like, but those work for me. As I said earlier there is a place for head lamps working on projects but on deck and in the dinghy is NOT one.
For finding your boat in an anchorage I use Google Maps function for parked cars. It works brilliantly. Alternatively you can use a nav tool like Aqua Map and drop a anchor watch. Either way, you can have someone navigate for you while you drive and avoid other boats (or slow down a bit and do solo). On my boat I have a Davis Mega-Light that I can hang from the boom. Some models have a flashing mode that helps pick a boat out. I don't carry them on delivery as I'm paid to move the boat, not hang out, but they have been handy on my own boat. Some blue plastic wrapped around it helps pick it out without any possible confusion with nav markers.
Remember to update everything on electronics before you leave home so 1. you don't have to wait over slow links and 2. you know everything is stable.
NV Charts does an outstanding job in the French Caribbean.