Interesting post that Jake.

I can speak from experience that when we came to UK, way back in November 2002, it really was a "re-entry schock" for me.
I hated it and found it extremely difficult to settle down.
Didn't like the food, or the prices. The people looked stressed and angry and their behaviour supported that impression. Most people were dressed so casually and dishevelled it appeared scruffy.
Nothing seemed to function or operate as it should. Shop staff sullen and unattentive. Customer service non-existent.
Fast food outlets dirty, tables not cleared and cleaned, floors dirty and spillages left to get trodden around and sure did.
Excessive yobbish behaviour and lack of visible police presence made 'going out' unpleasant.....

Whoaa, I need to be careful I don't get stuck in 'grumpy old man mode' here

After time it's possible to recognise that just like other places the UK has both good and bad aspects. It's really a matter of personal taste. You might think it's great and want to move there, or you might be stuck in the UK think it's terrible and you'd like to escape.
High (and ever increasing) retirement age, too few public holidays, miserable weather and a soaring cost of living (not to mention extreme high property costs) have combined to leave the UK trailing most other countries in disposable incomes and quality of life.

Here in UK we are taxed until the pip squeaks, the quality of life is appalling, wages are shameful and crime is spiralling.
The criminals have free rein while law abiding people seem to risk being persecuted.
The overbearing burden of bureaucracy, absurd laws and nanny state interventionism (over zealous sticking to trivial legalistic minutii) makes the country almost unjust to live in.
There’s not much here for me to be cheerful about.

Now see what you did Jake, I wandered off into rant mode again...

Says it all I guess.

There was a time when I would have agreed that my wife would have found in difficult to adjust to day-to day life in the Philippines. These days, I think she can see the positives far outweigh the negatives.

Let's make no mistakes though, living in a different country and different culture does not sit well with everybody.
Philippine life may not suit everyone and may end in tears. There's a lot of learning to do and a lot of careful integration also.
I image that for folks retiring in the Paradise Islands one of the major issues will be boredom. That needs to be avoided and resolved either before arriving or soon after.
Make a better life is the pathway to follow.