When I learned about the situation, I knew I wanted to help preserve the family property and also create a solid investment for my future.

Aggressive growth versus wealth preservation. 

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.

Your post nails it—long-distance real estate investing really does crack open a world of possibilities!

For example 3 years ago it was maximizing returns and today it is about preservation of capital.

So actual benefit is hard to nail down until it's actually tested/required to provide protection in the event of a lawsuit. 

The stock account is tanking, you see no hope for it to return, and you want to preserve the remainder of the principal;3.

BRRRR also assumes you nail the rehab and refinance steps, which can trip up newbies if costs or appraisals don’t align.

The preservation comes after you have it to preserve.

Anything you post here or ANYWHERE on the internet is preserved almost immediately.