I personally have success in doing flips with my partner here in Ohio.

Lower risk, lower reward.Flipping by yourself or with a partner is more risk, more potential reward(also more potential LOSS).

You made the mistake of trying to treat her like a normal, honest person.

House-hacking today often has to rely on much greater lifestyle sacrifice than what I personally did 10 years ago, and requires strategies that would make me uncomfortable like rent by the room, or using local laws that allow Short-Term rental only for owner-occupants. 

Personally, local is best but without knowing more about you, it might not be a good approach.

There are also a lot of questions we would have for you personally regarding credit and liquidity.

House hacking will also give you some personal "property management" experience.

In return, try to bring value to this person.

In my experience, the water company will give the person paying the bill a credit for the overage caused by the leak.

Hi Sara, Ultimately, the decision to keep the property as a rental or sell it within the 5-year window will depend on a combination of financial, market, tax, and personal factors.