My friend ... he's only gone and done it!

[Terpe]

I'm holding my breath at the moment, as I too am thinking it was all too easy. All above posts are correct, and his wife has even been working legit in Germany for the past 6 months. I can give you even more info on how he did it when he arrives in 2 weeks' time. They say God loves a trier, and by God he did! Every way he tried he met resistance until he read about this way. He doesn't like living there in Germany and can't wait to get back here.

The SS route was always pretty popular route. Over the years the UK has tightened the rules in an attempt to prevent people using EU regulations in such a way that can be construed as circumvententing UK immigration rules.
It got to the stage where UK was actually given written warning that the ECJ would make a ruling. Not sure if that ever happened.

Despite all that though, In January 2014 UKVI implemented the now well known
Regulation 9 (Surinder Singh Cases)

For those considering that route it's essential reading and well worth reviewing that linked document.

It's a huge interest here in the forum to understand how your friend came to satisfy the regulations. Especially since he was self-sufficient and Family Permits are normally not issued on that basis.
Additionally, he was only resident in Germany for 8 months. Again not meeting the Centre of life requirements.

I wonder if UKVI considered him to have "transferred the centre of their life" from Philippines to Germany then on to UK. Seems unlikely, but plausible.

I'm also wondering if the recent rulings from European Courts against UK might have been a major influencer. Take a look here

Where third-country nationals hold a ‘residence card of a family member of a Union citizen’, the United Kingdom cannot make their right of entry subject to the requirement that they must first obtain a visa

Whatever the reasons I hope you can secure some very helpful information and find the time to share knowledge here

Your friend is a very lucky man.