The primary risks at this point would be       1) to your lender, the risk of a margin call.       2) To you; underestimating the true cost of a project and cost overruns      3) To you; legal risk of securities regulations if you partner looses money. 

I know it’s no longer legal to do wholesaling in SC but let’s say you have the money to buy the property and you can turn it around.

Consult with competent legal counsel to guide you regardless of your choice here.

One common approach is to form a legal entity, such as an LLC, where both of you are equal partners.

Definitely something to pencil out with a lender or broker.

@Zach HowardThere is no legal requirement for landlords to actually witness lease violations firsthand.

This is for basic informational purposes I am not an attorney and this is not legal advice.First, if you offer to purchase a property using a HELOC to fund the purchase you cannot later back out of the agreement because you couldn't find PML or investors.  

That said, we have traveled a lot and stayed in wonderful Airbnbs over the years and have always dreamed of creating an incredible experience for someone visiting Minnesota with a short-term rental as well, so we are definitely open to that idea and have some great experience as to what we know would provide an exceptional short-term rental experience. 

You've got time on your side at age 29, so you can definitely retire earlier.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.