I have never paid a contractor to look at a planned project and give me an estimate.

Potential to add as much as 7,200 sq ft from adjoining vacant property, but have not spoken with owner.Will be meeting with the planning department to discuss further considerations, such as height restrictions, etc., as well as types of businesses they're hoping to see more or less of.

I plan to keep this property for a long term with long term or mid term tenants.

@Daniel MeaseIf #4 is important to you I would actually go offline and build lending relationships locally no fintech is going to really care about you and your business they are trying to monetize and plan an exit.  

Plan that worked well for you?

Educate yourself on the local market, network with other investors and agents, and always have a solid plan in place before making any investments.Also, I recommend reading “Long-Distance Real Estate Investing: How to Buy, Rehab, and Manage Out-of-State Rental Properties” - I found it to be very helpful when I got started investing 2.5 years ago.

They can guide you on the notice to pay or vacate, ensuring you're on solid legal ground without inadvertently stepping over any lines.Consider a Payment Plan: Given the surgery situation, a structured payment plan might be a reasonable middle ground.

He plans to move back to Texas in the next couple years but I keep telling him he needs to buy a home he can turn into a rental property when he leaves!

Chicago is a great market for 2-4 units if that is the plan you have built.

@Russell Brazil their plan has the E & O insurance for $100.