While I'm not familiar with west-coast cruising versus east-coast, I want to highlight that the value of each toy is related to your cruising grounds... If you're cruising up and down the east coast (where there's good cell coverage in most anchorages, a lot of marinas where you can re-stock, strong satellite signals, etc), your needs will be quite different from sailing in some of the smaller Pacific island nations. Each of the toys you've listed has limited utility to a long-range cruiser (i.e., outside the USA).
Of the toys you've listed, here's how I'd prioritize...
1: GPS. Absolutely indispensable, as it will help you confirm your location on your paper charts while you maintain your log. Carry at least two- One wired to the boat, and a handheld backup for the ditch bag. It can (should) also be used to provide a location signal to your other instruments (Chartplotter, DSC Radio, AIS transponder, Radar display...) Be advised, however, that some of the charts you're going to use outside the USA haven't been updated since Christopher Columbus or James Cook drafted them- while your GPS may be correct about your position on the chart, but the chart may be wrong about the location of the rocks, reefs, or shoals.
2: DSC VHF Radio. For coastal cruising, the DSC function is critical for notifying the authorities what to look for when you run into trouble- IF you've registered your vessel/MMSI properly, and programmed your MMSI into your radio. If you skip either of these steps, you may as well be using an old hand-held VHF radio. As an added bonus, it does allow for discrete contact with other vessels... provided you know the other vessel's MMSI (See: AIS).
3: Chartplotter interfaced with GPS. This does not relieve you of the need to maintain a plot on a paper chart, but it does make preparing for a journey and tracking your progress much simpler/more enjoyable. Fair warning, though, I have experienced finding items on a paper chart that my chartplotter didn't cover, like military training areas, names of bridges (useful when hailing for an opening!), and names of smaller islands.
4: iPod with all the apps. Once you leave the USA and a dedicated internet connection, the utility of all the apps should be re-evaluated... Having said that, the MORE important reason to have the iPod on board is to provide music/podcasts for those long watches. It can be plugged into the ship's entertainment system, or if the crew is trying to sleep, used on deck with headphones so they can get much-needed rest.
5: AIS Transponder. All commercial traffic is supposed to have this on board, but I'm not sure how well this is enforced in the smaller Pacific island nations. Where it will help you most is when you're looking at the nav lights of a freighter bearing down on you at 14 knots in the middle of the night, and you want to call them on the radio-- At least you'll know what name to hail, and stand a good chance of getting a response. If you have a DSC-capable VHF, you should be able to get the other vessel's MMSI from their AIS broadcast, which you can then use to make DIRECT contact with that vessel using DSC (it sets of an alarm on the other vessel's VHF when you hail them). Please note that the transponder sold to 'yachts' can be filtered out of the commercial vessel's display- so even if you have a beacon broadcasting your position, there's no guarantee that the commercial boat sees you.
6: XM WX. Useless outside the US, Canada, and the western Caribbean. IN those places, however, I view the satellite radio as indispensable entertainment... and the WX functions could be very useful indeed, IF YOUR CRUISING AREA IS COVERED. If not, well, I'll just enjoy the music after I've listened to the NOAA broadcast on my VHF.
Now, here are a few things that should be added above either the iPod or the AIS transponder:
a: A 2-Way GPS Communicator, such as the 'Spot' or the Delorme 'InReach'. They sell retail for about $250, and require a service plan with a monthly fee... but can broadcast a distress call from literally anywhere in the world (provided the unit has a clear view of the sky). The distress calls can be sent to a limited group (you set it up before you leave shore), or to an official emergency response agency. Some units pair with smartphones to allow text messages and facebook posts...
b. Good instrumentation aboard (Speed, wind, depth), with handheld backup units. The handhelds should go in the ditch bag, and the fixed-mounts used for navigation.
c. A working autopilot or wind vane. James Cook and Christopher Columbus had dozens of people to stand watches; on your cruising boat, the guy on watch may need to do something besides steering the boat. If possible, carry a spare drive unit and mounting hardware.
d: LED Lighting. I've replaced most of my fixtures with LED; I can turn ALL of my LED lights on and still use less current than just 2 of the old incandescent lights. Given the amount of OTHER gear we're trying to power

, we should probably try to cut back somewhere else.
Of course, these are all my opinions... As always, your mileage may vary.