Hmmm, I guess if you have deep pockets and big cahones now is a good as time any time
1) Only gamble with what you can afford to lose
2) Adopt a strategy and stick with it i) stay in for the long term years or ii) ride the market but this is a 24/7 watch
3) best piece of advise I was given "never be afraid to take your profits", seems obvious but +10% profit on today's rising stock may be tomorrow's 20% free fall
4) You are subject CG tax on profits, but get a good accountant as you can counter this with any losses
Alternatively you could look at investing rental property as the returns are typically 7%-8% at the moment