Proximity and identification of higher worth asset pockets becomes difficult/volatile to predict.Political environment and societal expectations that can be borderline ideological with regards to the aboveIf the crime does not get under control (see the above thoughts on education, gini, poverty, etc) this will weigh on perceptions and asset values for years to comeOn the upside:Indy is positioned well as a logistics hub which fueled growth, and it has a reasonably diversified economy.There is access to high quality higher education in the area.I will not invest in Indy although I did look at it awhile back.

Or should we operate as sole proprietors and use liability insurance to protect against lawsuits and have access to conventual loan sources? 

be organized.Example:3 months goalEnroll in real estate class-network and meet at least 3 real estate related professionalsSave XXX dollars toward first purchaseWork on marketing strategy, and overall strategy (define markets, focus will be SFR, buy and hold with 150.00 cash flow etc) 6 month goal--pass real estate exam--Save xxx--Improve credit score from 675 to 745make these goals quantifiable and specific, in other words you can cross them off when you get them done.The plan won't be perfect buy it's a plan and you show you are executing on it. 

Even if the rent covers the carrying costs he could still get crushed taking into account vacancy and future capital improvements/special assessments.

I don’t want to lose access to the house when I need to stay there but I also don’t want them there longer then a year if they can’t purchase the property.

I am a licensed realtor in PA, so I have specialized skills in other obvious areas of the business.We have a few approaches that we've considered in how to deploy our money for it's first cycle, and would appreciate some feedback from those with greater knowledge.Between our liquid assets and access to loans, we have the option to spread our nest egg out over several projects.

I don't have a real estate license so I can't access the MLS.

title insurance is like any other insurance you only need it when you acutally need it.I have a access claim going now 3 years probably 50k minimum title company has spent ..just the cost of doing business.Only time i would consider not buying it is say a tax sale or other very cheapo type properties that i had no intention of borrowing against or reselling.. buy and hold forever and then dispose of when done.

You are on right path to rent out other room, and to make improvements to your current home.

However, housing WHERE you want it, HOW you want it, and at a price YOU want to pay, well that's goes far beyond a "right".There have been many many solutions presented to improve housing affordability, like revamping our asinine building codes, reducing the cost of litigation, rewriting insanely punitive legislation such as the CRLTO, providing tax credits or reducing taxes, and increasing subsidies while reducing the red-tape associated with using those subsidies.