So it's a gamble.

The stocks to me are similar to a gambling

If you want to refinance in less than six months, you need to use the delayed financing program, and you should be familiar with the guidelines before you start, and even more importantly, you need to find a lender that is familiar with them, which I have found to be the real challenge. 

Normally"  when you are new to real estate investing the typical guidelines for a "newbie" are: 30% Down Payment + Closing Cost + Reserves.   

On a one-off case-by-case basis underwriters will sometimes work with the change provided the time since restructure plus time before the restructure adds up to 2 years (your anecdote quite possibly being an example), but the income they calculate is generally less than if there wasn't an attempt to circumvent the guidelines. 

Roommates are always a gamble but usually more profitable. 

When you reach out to one lender, you're stuck to one lender's rates, terms, and guidelines, along with the products they offer.

Your equity is in jeopardy in a SFH at this time.Others will have a opposing opinion but do you want to take the gamble of holding if you already know that you have likely maximised your appreciation for the foreseeable future and risk a market/equity drop.

Fannie Mae has strict guidelines on what they'll accept in rent to own contracts and it was looking like my best case scenario was using the $8,800 to lower the purchase price to $138,200 and get an FHA loan.

Again check your convenants for those guidelines.