@Salvatore Amato appreciation is usually lowest in C/D Neighborhoods, relative to the overall local market.A bigger concern is how well you understand all the challenges!

I know leasing a LTR in Chicago can be challenging in the winter, is the same true for MTR? 

A combined approach of a short app and sending a link to smart move or rentprep or similar can give you a good picture.

Since the internet wasn't really much, it was a different approach to finding properties "Off Market" (or was it) Do you know you can pay $20,000 less for a house when there isn't a real estate agent?

We bought it, renovated it to meet sober living standards, leased it long-term to an experienced operator, and then refinanced once the home was stabilized.The challenge was getting the refinance done.

A few quick tips:Wholesaling first: Great for learning deal flow without risking too much.Keep the winners: Deep discount, high-cash-flow deals are perfect for building your own portfolio.Mentorship matters: Find someone actively doing deals, not just teaching courses.Watch pitfalls: Compliance, team management, and local market demand are key.If you execute well, this approach can set you up to scale smartly.

Deals like this do exist on-market, but you just have to be able to recognize them.If that’s challenging, it’s important to work with an agent who understands the market and can help identify opportunities, like I do for my clients.

When comparing notes to investing in traditional real estate, I'd say one of the biggest challenges is the note investing can be a more capital intensive business, requiring more money upfront with less creative strategies for an individual to buy (though you're always buying at a discount).

Perhaps the less eyebrow raising method would be, if your goal was a more hands-off approach, is to leave it as an str the following year but under full time management, once your material participation hurdles are met in the previous tax year. 

Challenges?