Preparing for Retirement Move

Sorry if this open-ended, but I could use a kick start for organizing and conducting my move to the RP.  No matter how many tasks I write down and start on, the task always seems daunting.
I posted in my introductory post that I am planning to move to the RP for retirement within a few months.  I also indicated that I have conducted a couple of reasonably recent recon trips.

I would benefit from a list (and schedule - to do things in the right order) of tasks for what to do and prepare for.  I have read about getting health insurance, getting a Schwab account for my investments, and will be scouting hotels to stay in immediately after arriving while I seek out more permanent housing.

If posters here know of existing lists of this type, whether free or not, please feel free to link to them.  I don't mind spending some money on this type of thing, if someone here has a favorable review of the list in question.

A few questions that spring to mind:
Regarding the move itself:  what type of possession would you recommend shipping over, and which would better be re-purchased in the RP.  I've read that in many cases, the quality of U.S. housewares (kitchen appliances and the like) that U.S. products are better and that equivalents might not be available in the RP.

Document scanning:  I have medical, financial, and legal records that fill 4-5 portable plastic file boxes.  Any recommendations regarding how to best handle this information would be helpful.  For e.g.: scan and store on the cloud; store the paper itself in a local locker?;

Limited cargo on initial flight out:
If one or two boxes are particularly important to me, would it make sense to pay to bring them (if this is even possible) on my outgoing flight so as to not have to wait months to receive them?

It seems like a no brainer not to bring books??

Sorry if this rather detailed.  But, I've read of people who fly out to Manila with only a suitcase, and others who seem to ship entire homes' worth of stuff.  I'm somewhere in between, though closer to the suitcase option.

My 2 cents is that you sell your household and simplify and minimize.  It allows much greater freedom and for the cost of shipping you could already set up a new household here.  For me simplifying my life was part of moving overseas...why bring all the baggage and hassles with you?  Then again I'm happy not to live the “American lifestyle” here..less is more.... so this is obviously a decision each of us needs to make.

As to important documents I would scan and upload into the cloud.  Medical is covered locally with PacificCross and I have an additional international plan.  If you qualify for Medicare you can decide about a medical evacuation plan only. 

Where are you looking to move to in the Phils?

Minimalistjourneyman:  I'd like to complete the move within a couple of months.  Just having trouble getting organized.

A customer service rep for my Medicare Advantage (MA) plan told me that I could keep my MA plan active so long as I return every six months and re-establish my residency locally (for however short a period).  MA won't pay for day-to-day medical expenses, but can be used for emergencies.  So I am considering keeping my MA, and returning home (Washington state) every six months.

Yes you are correct on Medicare Advantage and part D.  For Medicare Part A and B you don't need to reside in the US.  That seems burdensome to have to travel every six months.  If you are determined to get US care that may be your only option.  There are international plans that offer care throughout Asia as well as at the best facilities in the Philippines...not cheap if you are over 65 but probably not too much more if you factor in travel costs.

I agree with the idea of keeping it simple, you can probably take two 23 kilogram, 50 pounds, suitcases to fly in no extra charge.  You plan to keep using Medicare you might want to check out Guam, a lot closer to the Philippines than the West coast.  You also might want to check out Balikbayan shipments from the West coast, especial if there is a Filipino community in or near where you live.  If we deliver the boxes to New Jersey they are shipped by sea, takes 90 days, longer near Christmas, and costs $45/box.  A lot of books are not available in the Philippines,  BB shipping is by volume, not weight, so you can get a lot in a box.

Mugtech:  My current landlord is Filipino and will beliving in the Seattle area for years to come, so I'll be investigating this further.