So, we found one or two that were hungrier than the rest and had a desire to grow a family business, one where we'd be giving them the work.

I.E. using all the equity available breaks the DTI ratio for the desired loan?

Sounds like you have a good understanding of the strategy.I normally work with clients by giving them a price range of a property they need to buy to get to their desired tax bracket.Best of luck.

I had desisted of the idea of house hacking due to the fact that most small multifamily properties are  the most desirable areas(based on my experience).

Name = Jonathan KlemmExpertise = Renovation & ConstructionLooking forward to = In-person Networking / Vacation in the sun (getting away from the windy city Chicago)Connection desire = Someone who has scaled a service business to $100MSession = Flipping houses in high interest rates, but I am biased! 

Less desirable and by no means luxurious but not dangerous, no intensive management needed, properties unlikely to appreciate much over time but very attractive from a cash flow perspective.

Identifying those opportunities can lead to solid investments.Demand for Affordable Housing: The points you made about the demand for older, well-maintained properties in desirable locations are crucial.

I am in the camp that anyone can be found rather easily but it's a choice of your comfort level and what your desired outcome is.  

I have no opinion about Ohio other than I have no desire to invest there. 

As long as you have the desire to keep going and learning that's all that matters!