Quote from @Scott Tennell: What creative financing strategies have you found to be the most effective in today's real estate market, especially in terms of working with sellers or investors in challenging conditions?

After identifying the property’s potential, we negotiated a competitive purchase price of $28,000 by highlighting its renovation needs.

Make vacating the unit a condition to close in your offer.

This would be primarily due to your competitive advantage of living in Chicago and knowing the market.

If forced to cure - and it will be a condition of remedy - the tenant can take action against you for damages from leasing an illegal property. 

I am leaning toward placing a competitive offer.

I find myself spending a little more off season than on as I do more tweaking and research to remain competitive and in front of eyeballs.  

There are inconveniences to investing out of state like traveling to see properties, meeting with contractors, checking work, checking the property condition.

But most pricing is a function of recent comps, adjusted for the subject property by size, condition of systems, and aesthetic qualities. 

The STR regulations are very black and white and I don’t see many, if any, clients having issues with obtaining insurance if the house is in good condition.