The question is take a bit of a gamble and learn the business through joining the Brokerage Team?

Now, I am not one to risk big $$, but IF I were a gambling man, I would jump on the condo (at 50% on the dollar of course:), get the place cash flowing, and if FEMA steps in, you just doubled your money thanks to the American tax payer.

Without this large influx of cash it'd take you 10+ years saving 10% of your annual income to get to that amount and you're willing to gamble on a go big or go home mentality?

But I cant gamble like that so I am acting as though that wont happen.

Take a gamble on birdtown for cheaper property? 

I'm feeling lucky, would buy a lottery ticket, but gambling without free drinks just feels wrong.

Many wholesalers now are just doing robo calling and trying to get folks on the phone I get one to two of those a day.. most I don't talk to some times I will .. many of these are using off shore call centers so semi broken English reading form a script.. but they produce leads.. its just like buying a car.. the sales guy ( telemarketer) then hands you off to the closer.. then you have the I buyers backed by wads of VC money big advertising budgets and super sophisticated web sites that spit out automated offers.. the business is changing no doubt.. and there is no doubt like Will Bernard stated its probably the toughest thing in real estate to master ergo 9 out of 10 never get past first base.. 

If I want to make a charitable contribution I will give one instead of gambling with the money.

Be sure your end buyer is going to show up and/or be prepared to lose your EMD.If you don't have the cash to close remember what you are doing - you are gambling with your EMD - you are going to the tables and putting $X down on the buyer - the buyer doesn't always show up.So - yes it is possible to do it - if you have a title company that is ready willing and able to do it.The fact that you say you can buy in your LLC and then sell the LLC leads me to believe you have the cash to do it - that is a good thing - be prepared to own the property yourself.

It is always a gamble you take on any offer you accept.BUT -- to reduce your chances of the buyer not qualifying for a loan, ask to have the buyer cross-qualified by a lender you know, like and trust.