I'm planning a similar venture living in the Denver area and purchasing in the Green Bay region but we've got a ton of family in the area and will have boots on the ground to help. 

Many OOS investors set themselves up for failure because they don't truly take the time to understand:1) The Class of the NEIGHBORHOOD they are buying in - which is relative to the overall area.2) The Class of the PROPERTY they are buying - which is relative to the overall area.3) The Class of the TENANT POOL the Neighborhood & Property will attract - which is relative to the overall area.4) The Class of the CONTRACTORS that will work on their Property, given the Neighborhood location - which is relative to the overall area.5) The Class of the PROPERTY MANAGEMENT COMPANIES (PMC) that will manage their Property, given the Neighborhood location and the Tenants it will attract - which is relative to the overall area.6) That a Class X NEIGHBORHOOD will have mostly Class X PROPERTIES, which will only attract Class X TENANTS, CONTRACTORS AND PMCs and deliver Class X RESULTS.7) That OOS property Class rankings are often different than the Class ranking of the local market they live.8) Class A is relatively easy to manage, can even be DIY remote managed from another state.

We’ve got an STR in Oak Island, has been a successful venture thus far.

For those of us that started a business venture of any kind, was your personal financial position solid when you started?

You can recover from "stranger danger" much more quickly than you will from a friend who doesn't know what they're doing and does you a "favor".This one really aint DIY - Re-read Steve Vaughn's post again about finding competent representation for his 1031s..    

I was planning on house-hacking and renting out the mother-in-law duplex basement (more updated than the upstairs), and rehabbing the upstairs while I live in it, some DIY and some contracted out.

@Max Kats This is the great thing about joint ventures.

Even if you're planning to do 100% of the work yourself (And I hope you're not), materials alone will blow your budget by a lot.Just looking at the pictures you've put up, I'm willing to bet there's some DIY electrical.

This first subsidiary's purpose would be to invest in such products as stocks, mutual funds, REITs, and other brokerage services to build capital for the venture.

Charles village is one place where condos might work but I still look at it as a high risk venture.