Are people just willing to gamble that the first trust Lender will allow their lien to be extinguished?

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.

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’ve immersed myself in the podcasts, books, etc, and am excited to learn more from this community.

You really need to immerse yourself and learn all you can.

I recently have been immersing myself in the real estate world (podcasts, websites...etc) and would love to become an investor and rental owner in the near future. 

Before doing so I have been thinking about getting my RE license to assist with deals and immerse myself the market.