My two cents on some of the issues discussed-
As far as the EPIRB/PLB debate goes, both have their merits. Kevin is right that with the PLB, you can take it with you should you go on a different boat, and be perfectly in regulation. (Frankly, you can do the same with an EPIRB; it's not ideal but so long as the person you have listed as your primary contact knows what's going on and can point the CG in the right direction, it's still going to send a locating beacon regardless of what boat it's on. Whole lot better than not having one.) Other advantages of a PLB are size and cost for battery replacement. What an EPIRB offers over a PLB is twice the battery life and the ability for automatic release and activation. Also, should you end up in the water, an EPIRB will float upright and continue to broadcast, whereas a PLB will need to be held upright to broadcast, and if you'be ever tried holding something upright at arms length for a couple hours it gets pretty taxing. I'd stay away from the SPOT as a primary distress beacon, personally. The battery life isn't as long, the distress alerting is less streamlined, the positioning data isn't as good, and it also has to be held upright. Plus, does your wife really need to see that you and your son are sitting out over your favorite fishing hole? Not to mention if you're running it continuously, it'll either need to be plugged in or you'll be running the batteries down in case of an emergency. It's a cool toy, but not what I'd consider primary safety equipment.
The inflatable vests are a good choice, but I think I'd save the cash for the extra "fanny pack" inflatables for in the cabin use. My choice would be, unless you find the inflatables to be prohibitively uncomfortable, wear those instead, as they're a better vest. Instead of buying the fanny packs, I'd HIGHLY recommend purchasing a GOOD Type I life vest for every person you intend to take offshore. Those little Type II Walmart horse collars are a JOKE if you have to spend any time in the water; and if things ever go really south I'd be reaching for the Type Is over an extra inflatable. Type Is will turn a person upright in the water without effort to maintain that position, which is a big factor in conserving body heat and avoiding hypothermia. They provide significantly more buoyancy too.
Totally agree with Kevin on the 25/12 flare gun. You can load up on cheapo 12ga red star shells and have a few parachute flares in the 25mm for the staying power. I'm a mariner by trade, and trust me, you CANNOT HAVE ENOUGH aerial flares if you're trying to get a ships attention at night. We can't look in every direction at once, and things that seem bright on land lose a lot of intensity over long distances at sea. I carry somewhere around 20 12ga star shells; plan on using 3-4 for any ship that you're trying to alert. The CG requirements for pyrotechnics are absolutely laughable.
Other things I'd make sure to have: first aid kit (obviously), but take it apart sometime and see what's really in there. Better to be familiar with it then to be fumbling around when you need medical supplies.
A dry bag full of towels, blankets, and warm clothing, if you have a MOB situation or end up picking up others that have been in the water, you need a way to warm them up. They can be stuffed in a locker until needed, or used as a cabin pillow/napping supplies. I devised a bungee cord system across the inside slanted portion of my cabin overhead that holds my 6 Type Is, some rain gear, and my towels/blankets and such.
A decent portable spotlight that plugs into the cigarette lighter because no matter how hard you try you'll probably forget to keep a rechargeable charged (unless you're a lot better with that stuff than me :lol
Even if you don't intend to be out at night, there will come a time when you stay out a little longer for a hot bite and then need to pick up buoys in the way in, and a permanently mounted one is actually more difficult to use than a handheld. Plus it'll likely crap out on you at the WORST possible time.
Look at getting either a Lifesling throwable or a rescue heaving line; liferings and those float cushions make you legal, but they do nothing to help you get a MOB back to the boat. Either way, PRACTICE throwing it, it's not as intuitive as it seems.
A handheld VHF is a good addition to a ditch bag, especially one with the option of a AA battery tray. Several manufacturers make one with a GPS so that takes care of position data unless you want the redundancy of a backup GPS navigator, in which case there are lots of good inexpensive options on the market. Keep spare batteries on hand in either case.
It's pretty much impossible to have too many flashlights. Buy a bunch of mini-led maglites and stache them everywhere. Same goes with folding STAINLESS knives.
Get a good tool kit. The ones sold as marine package deals are usually ok, but keep in mind you'll need to supplement them. A hammer, vice grips, several bigger adjustable wrenches, any specialty tools, plus the usual staples of duct tape, assorted zip ties, electrical tape, hose clamps, and shop rags, and you can address damn near anything.
And, last but not least, a towing insurance policy, in case you're past the toolkit but not quite at the EPIRB. :wink: