Once you leave the small circles of high school and college man your life is your own adventure.

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

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.

I make about ~$60-75K/year (bonus dependent) as a market research analyst focused primarily on the regulated US online gambling industry. 

Thanks @Tom Ott, I plan on making the most of this adventure.

Can't wait to learn and start my adventure into the real estate. 

Quote from @James Gamble: Quote from @Joe Summer: Quote from @Greg O'Brien: @Luis Espinoza I would say you are better off finding a good asset protection/biz attorney and CPA combo.

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

Linval thank you for all those articles, just finished reading them all, very excited to start this new adventure.

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.