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| Episode | Episode Name | Air Date | | 1 | A Family Affair | Fri Jun 02, 2017 | | 2 | Brotherly Luck | Fri Jun 09, 2017 | | 3 | Lake House Lottery | Fri Jun 16, 2017 | | 4 | A Fairytale Fortune | Fri Aug 04, 2017 | | 5 | A Mexican Dream | Fri Aug 11, 2017 | | 6 | Dreaming Big in Boston | Fri Aug 18, 2017 | | 7 | Mom's Million | Fri Aug 25, 2017 | | 8 | Deano and Carissa: A Scratch Made in Heaven | Fri Sep 08, 2017 | | 9 | Gail and Chet: Boston Dream Garden | Fri Sep 15, 2017 | | 10 | Gone with the Win | Fri Jan 05, 2018 | | 11 | A Million-dollar View in Orange County | Fri Jan 12, 2018 | | 12 | The Maine Attraction | Fri Jan 19, 2018 | | 13 | The Luckiest Cape | Fri Jan 26, 2018 | | 14 | A Family Fortune | Fri Feb 02, 2018 |
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