Establishing the LLC in IL first does not provide any additional benefits in this scenario.

Ok it might not be 1:1 but it will add additional revenue.

The additional bedroom adds to both the rental value, and significantly to the appraisal value, obviously.Given it's priced as if it's a 2 bedroom and not a 3, it seems like a great deal. 

As a landlord you might want to go with a cheaper "named perils" policy instead of a comprehensive homeowner policy.I guess the good news about your HOA fees is that you're not being hit with an assessment in addition to higher fees. 

  $128 would be lowest monthly cash flow I've received (currently have 5 rentals), but I'm focusing on the $30,000+ in equity in this deal. 

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

In addition, trade policies have introduced new cost pressures, with a 10% tariff on Chinese imports raising prices on certain goods, though tariffs on Canadian and Mexican imports remain suspended until March.

These are professionals with additional training and a stricter code of ethics.

With your considerable experience and, I'm assuming, strong credit score, you would be well-positioned to receive high leverage and low rates from most private lenders.

@Joe Michaels, What a lot of investors will do is to use the 1031 exchange as @Michael Plaks said, isto actually "acquire" additional depreciable basis.