2nd piece is the house hack...We think best course of action would be to have an investor friend we know buy the house in cash, once we are done with renovations, we then take out a full mortgage on the house to cover whatever he paid for it and then pay him back with some interest.

You should consider that the moment you start a business you will be subject to self employment tax which is something like another 15.6%Are you assuming that owning a rental property automatically implies you will be cash flowing positively because that is something you have to make sure of and there is certainly no guarantee about cash flowing positively.

When you use your money (cash flow and personal income) to pay down any debt that the tenant is paying (thanks to positive CF), you are adding to what the property costs YOU. 

FWIW, I found that having a partner allowed me to get out of my comfort zone a bit and work through "paralysis by analysis" and take action.

I will keep you in mind if our position changes. 

I've heard there is an appraiser in my area that will possibly only use the income approach with this but I haven't used him before (this being my second deal) so I'm not positive.

@John Woodrich we do have a positive migration

@HAILEY ERSKINE I think in your position, you may be better off to do a virtual wholesaling.

Perhaps the best course of action is to continue learning about real estate and look for deals/network.

You already did the hardest thing, which is taking action.