"I bought another house today" to them is a gamble I just took, to me its at least $25k already in the bank.  

Probably not but are you willing to gamble that?

It's so much money on a huge gamble. 

It is a gamble!

I am originally from the UK and have lived here in Orlando for 18 years.

A guarantee to lower the price is simply an invitation to raise the price as high as a seller can, with or without adding any value, and gamble on an appraiser bringing in as high a value as possible.  

;-)I realize that property prices in Singapore, and many other markets around the world (UK, Australia, etc) are very high.

This seems like a reasonable gamble.

Many people are gambling on the market.Fund managers are having a party with cheap money floating around everywhere as well.I'm very conservative and young, so if I have to wait until the end of the year or into 2014 for a correction to buy back in that's OK with me.

The banks know that these 30 year FRM (fixed rate mortgages) only factor interest monthly so paying extra like the above comment mentioned "does," save you interest but its only factored 12 times a year so instead of daily savings differenials you're waiting all the way till the next month for your lump sum payment of lets say $2000.00 to affect your amortization of your loan.The HOA product was originally started in Australia/UK and gradually came over but is still lesser known gem when used correctly.