I have been eying Indy as well. you have great points!

Plus, keep an eye on emerging markets like Greenville and Columbia in South Carolina—they’re seeing more development and interest.I can get you more information on specific areas once you have a more concrete idea of where you want to invest.Let me know if you want to connect and I'll be happy to help. 

After about 6mo I ended up meeting the love of my life which opened my eyes to thinking further down the road than I had been previously and although I really enjoy the Casino Marketing game, I soon realized it would not be the best path to achieving my life/financial goals for my future family.

Assuming you are the single member on the LLC, if the property holds the LLC you would not be a first time home buyer in Fannie/Freddie's eyes.  

The experience of generating consistent cash flow from that rental property opened my eyes to the potential of leveraging real estate as a long-term wealth-building tool.

If you need assistance with eyes on the ground, resources or companies to work with, my suggestion would be to get on here and be transparent just like you were with this post. 

We don’t feel great about it for various reasons, namely it’s a liability, an eye sore, and we don’t know of all the problems this could present.Has anyone had this happen?

Just wait until you or someone you love becomes disabled and you'll find yourself viewing those funky features with new eyes.

If the numbers work, I think it makes sense to do it while you are still there, learn, build systems, have a handyman, and then have your parents be your eyes and ears, not a PM.

Bringing your family along also puts a serious damper on that the primary purpose of the trip was actually for business - not impossible, but in my eyes it definitely taints it in a way that you really want to ensure everything is buttoned down on the business purpose and the actual business activity that occurred.