There is a part of me that is crazy taking that gamble. 

The thought was to utilize the twelve months and utilize as much as possible take the gamble that I can get two done with one fee

You being a commercial RE broker you may have people who like you with deep pockets who are willing to gamble on you as a newbie to real estate investing.  

Planning on an area turning around is gambling not investing.

Something recently shifted with our new business and in order for it to avoid any appearance of being illegal gambling, we need to prove the business has $300k (which will not be spent, it will just sit in an account to prove its existence).

If you don't know the market you are trying to get into you shouldn't gamble it.

I'll continue my learning and saving and not gamble with the gift.

while its a gamble to count on appreciation it makes little or no sense to me to deliberately invest some place that has a slim chance at best to appreciate. 

But, this of course is another gamble.

To me it seems you're speculating or just plain gambling on the market.