Since my aunt is the listed owner, Proposition 19 does not apply in this case.We consulted a lawyer who mentioned that transferring the property to an LLC could allow me to be added to the title without triggering a property tax reassessment.

I'm with you that sidewalk slip and fall litigation may be less likely in the Midwest than say Mid Atlantic which tends to have more litigious cities but dismissing premises liability issues can come back to bite an investor and when these properties have such razor thin margins that an investor must consider the cost benefit analysis of safety against ROI, there is a real estate issue and is usually a losing proposition.   

I work with a lot of househackers and they're typically on the 12 month cycle, rinse and repeat.While the proposition of acquiring an investment property outside of your market in a "landlord friendly" state may sound appealing, i would recommend you stay local for now and househack another couple of properties over the next few years until you've got some more time / experience under your belt.you would need a management company to cover your property that is outside of your market which would not only take 8-10% of your gross it would also leave you a bit vulnerable to a property management company that you A.)know nothing about and B.)you won't have the experience or cashflow or proximity to deal with any headaches that may arise.i would recommend staying local and househacking your way along for now and then maybe hire a local property management company initially to work with your current/local properties to get a taste of what to expect if and when you begin investing outside of your market.

If your goal is financial freedom, which is a long-term goal, not so much.Financial freedom is a long-term proposition, not a one-time event.

This can become a selling point or value proposition for your future clients. 

Sometimes when examining the entire capital stack, its determined the higher finance charges paired with higher leverage is a winning proposition but only experienced real estate investors should be making that call. 

Buying real estate without debt is not a very attractive proposition for investors. 

I would say hire another you when your value proposition begins to slip (e.g. you can't stay true to your boutique goals because of the volume of work) or when the work is too much for you alone.  

@James Zobrisky Relying on cash flow to fund future acquisitions is a challenging proposition.

@Greg P.There are a lot of unknowns in your proposition.