and if so, what kind of hurdles should I account for in planning my strategy?

My question is, what kinds of things should I look to improve, and how do you stop yourself from going further?

I understand that your wife may be worried about failure, but any kind of investment comes with a chance of failure so the risks must be understood prior to jumping in and the fear must be overcome with the confidence of being successful.Since you're starting funds are $0, a HELOC can be a great tool for getting started, but ultimately you will need some kind of funds of your own because you must pay the HELOC each month during the flip.

Detroit has one of the highest crime rate in US (less safe than 98% of US cities ) .Myself live in Canada, but have visit Michigan many times, for me I am looking at Warren as potential city, but still need input from others as I am also trying to decide which city is the best for investment . 

It's a relative, well an In-Law for me, who wants in...they have nothing...this would be like, be their shot out of minimum wage forever kind of stuff.

You might get more since it has some kind of barn on it.3.)

Good job being open to this kind of experience so early.

The owners who offered the seller financing deal are very busy people which I get,but with my lack of capital or resources im basically sitting around waiting on them to make a move.I specialize in owner financing deal structures - what kind are you wanting to do?

I'm kind of house hacking (using rental income to pay a mortgage on another house), and am interested in purchasing multiunit properties.

It all depends on what your investors are looking for.Sounds like you haven't settled on what kind of purchase you want to make.