So we have chosen RE as the vehicle to get us there.  

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.

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.

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. 

That is a losing gamble in my opinion.I agree that a recession is in our future, but I don't think it will be a house buying opportunity.

You could not have chosen a better area of Florida to stake your claims.

Couldn't pay me to gamble on the outcome of that mess.

I usually have my assistants watch over the rehabs and make sure that they are being done correctly with the paint and flooring that I have chosen, etc.