My brother's singaporean brother in law did just that years ago... he sold his condo becuz he thoght prices will collapse, mana tahu prices still got legs to run.  Then he had to squat with his mother in law while waiting to buy his home.

I think, if you are married with a family, NEVER sell your home.  If you want to invest, you may consider refinancing your home to get some upfront money, provided you have enough cash to service instalments.

Property investment is for the long run.  Dont think u miss out if you dont jump in now. 

Also, you start small...  Renesial recommend for small timers to start with apartments that are below 100k. 

Be patient...  if you rush it, you will give yorself too much stress and it is bad for health and overall well being of your relationships with others.....