Yes PH, I entirely understand. You start out small-time, and get on with your life and career, then years later turn around and think, jeez, well, that worked out ok, but now I’ve got most of my eggs in one basket: Is this prudent?
That was my thinking behind starting to build a stock portfolio (just passive/stable, in the background, keep on reliably chugging along, without paying 5% pa year-in-year-out to ‘advisors’). It was and is a counter-point to
property.
Again you need to define your investment objectives. I’m as guilty as anyone else about being complacent at doing this (‘It bores the tits off me’ as one might say in England

)
I’ve a few properties (rentals) and my current thinking is a ‘great rotation’ lol. I.e. I have really 95% had enough of the bulls*** involved in being a landlord, especially the random stupid, weird stuff you seem to have to put up with. The f***tard surprises really piss you off exponentially more as you get older. 20YO tenant and 30 YO landlord, ok, vs 20 YO tenant and 50 YO landlord .... lol!
Is it time to forego property’s historic climb, for a simpler and less stressful life? Tricky. I told my (trusted, and long term agent, about my pondering and their stark reply was ‘Noooo!’. I do not take that lightly! But also accept that as much as I trust them, they still have their self-interest). The thing with property is that you can do it on margin, and 75, 90% mortgage? Sure, maximise your leverage, as long as it keeps going the right way.
But how much is enough? There must be enough. There must be a goal. When do you take your accumulating chips off the table? <conundrum>

. I think someone recently accused me of gloating, for floating this question before, but that is misguided. For every me, there are 99 people in SG with way way more than I will have. I’m not out to show off (sitting here in my $2 boxer shorts and freebie $5 value casio watch lol [it’s good though!!]). It is more of a philosophical point. And it is perhaps like a roulette player, having had two good plays, then asking, ‘what do you think guys, how far do I run this?’
Most expats here are like roulette players. They've put their chips on the table, and are running a risk position. ...
Right now, having been Non-UK-Res for 5+ years, I can sell, and not be liable to CGT. Bingo! (you might think) That’s a big draw, that sits in line with trying to simplify our lives as we errr ... mature
We will probably return to the UK, either in 2014, or ?? if we get one last posting out of here [intentionally vague].
Now, if I can stick the assets in a brokers a/c (tax free) in the Isle of Man or Channel Islands, or have Tracy the fat Aussie chav call me pi**ed at 2am demanding I somehow turn up to unlock her door... what’s it going to be ... phh...
.... Either way. This is just a major theme I’m considering, and contemplating. Moving from a long-term strategy of being leveraged and risk-on. To now, especially considering tax, moving towards being more risk-off, offshore (tax efficient), and passive...