I think that there's a spin to your post that needs to incorporate the idea of being "welcoming" and "encouraging" of every member to pursue the long-term benefits of real estate responsibly, even as we of course do not want to encourage irresponsible real estate investing decisions.Curious to hear other's thoughts here. 

Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

I'm based in California, whether you are a foreign entity operating in California, or incorporated in California you'll need to file a return in CA.

It’s the city limits of incorporated Blue Ridge that you can no longer get an STR permit 

I have registered an LLC and incorporated business with contractor license.

Did you have to incorporate a special tenant screening process?

I am incorporating several tree houses in a development I am working on and because they are such a unique experience I have found every tree house experience is rented out 12 months in advance and attracting top dollar.  

For the remodel I am thinking of extending the main home (which would make it "L" shaped") to incorporate the detached carport and detached bedroom/bathroom.  

A little about me:I hold a Certified General Appraiser license and have been working in corporate and commercial real estate for over 25 years.My recent focus has been on property investments and appraisal work, including commercial and residential properties, lease-to-own agreements, and broker price opinions (BPOs).I’m always looking for opportunities to expand my portfolio and knowledge in real estate, and I love analyzing market trends and valuations.I’m here to connect with other investors, share insights, and learn from the wealth of knowledge this community offers.

@Suhaib RehmanThere are investor platforms, such as Cash Flow Portal, that offers underwriting tools that incorporate AI and automation.