Don't gamble and hope the house will be worth more when you want to dump it, and even worse, if something happens and you find yourself having to dump it sooner than you thought you would, you've turned yourself in the motivated seller.

Staging is a gamble, but one that normally pays off if the home is priced correctly. 

dont gamble with your parents retirement. side note if you do this on your own you will be a better investor than if you were handed the money and you will feel more accomplished, good luck.

I work offshore on a 28 on / 28 day off rotation, I am looking to invest time and money into our future, is real estate investing a viable market?

No,you are not required to pay the buyers closing costs by the VA or any bank loan.It is a sales tactic.They are already getting a no money down loan from the VA and now want you to pay the rest of it for them to make it a home run of a deal for them.Simply counter to them by stating you will pay none of the closing costs.They are gambling that the house doesn't have any other offers and won't anytime soon and are trying to force you into making less money.Everything is negotiable.Offer 1/2 the costs if you want.Also remember that the VA is notoriously slow to fund the deals and escrow can take up to 60 long days to finish with no guarantee they will be approved until the end.

Website optimization was a gamble because of the cost, but on the buying side, it paid off.

I think the house prices will rise even more so people who pay a premium now will at least get to break-even, but that is gambling in my opinion and not a way an investor works. 

Any thoughts on whether this is more of a gamble than an investment would be much appreciated. 

Are there any advantages  with trusts such as  domestic/offshore asset protection trusts, etc.?

@Kevin Estey , I haven't used them myself but I always hear Matthew Gilligan's (at GRA) name come up when property tax and accounting come up in NZ so he may have a speciallist on the off shore tax questions.