@Grant Vincent I think what your Mom needs to establish is a "life estate" as you mentioned.

Now that I'm more established I wouldn't hesitate out of state investing.

I would also carry the loan and establishing a penalty for early payoff (how much penalty?) 

This is looking to be a more complex lending situation due to lack of relationships established, but I have to start somewhere i suppose.

If you can establish a team you trust in a market perhaps the team is more important than the market itself.  

I would establish a team in whatever area you choose.

My goal is to establish a well-rounded portfolio of rental properties that not only promise financial growth but also offer value and sustainability to communities.I’m particularly keen on understanding the nuances of different real estate markets, effective property management techniques, and strategies for making informed investment decisions.

here you go:https://www.redfin.com/IL/Bloomingdale/174-Merganser-Ln-6010...as you can see, it's the LOWEST priced land in this very established neighborhood!

I aim to establish connections that can support my business needs effectively.Could anyone share their experiences or recommend strategies for connecting with reputable wholesalers in these areas?

Look at true, regional, drivable vacation markets instead with established STR presence