The theory that Jonathan and Drew know a winning horse when they see one is put to the test when they decide between a historic property investment and a two-story blank slate. Both are equally promising, yet neither offers the path of least resistance.

The Brothers must decide between two experienced investors with much to gain, and possibly lose. One is taking on a massive flip with enormous value. The other is betting on a sophisticated rental triplex with the potential to turn a major profit.

After helping a newbie investor sell her late husband's commercial space, Jonathan and Drew continue their backing by reinvesting her profits into a residential property to generate much needed income, but they only have 45 days to make it happen.

Jonathan and Drew must choose between a rookie investor way in over his head on a massive, million-dollar flip, and a widow who's been sitting for years on prime real estate, all while racing to help a previous investor get his triplex back on the market.

Jonathan and Drew must decide whether to back an overwhelmed investor that is quite possibly sitting on a goldmine, or a flipping couple who secured an enviable property but have no idea if they should renovate for higher resale or rental income.

The Brothers face a tough decision between a pair of investors who have sunk all their savings into a flip gone wrong, and former spouses in a make-or-break financial position with hopes to convert their garage into an income generating unit.