@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.  

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

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.

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

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!

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.

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

If you are planning for both MTR and STR and are able to pivot to 100% MTR if things go south, you should stick with this city.

I plan to tell them the inspections need to be completed prior to any cleaning service or move in.