Additionally, I split my time living between Spain and the Netherlands, giving me a fairly broad perspective on both countries.

For a number of reasons we are going to need to make that jump fairly soon, so if anyone has made the move already I would be very happy to buy them lunch in exchange for their thoughts! 

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

If you're targeting Section 8 tenants in Chicago, I'd suggest listing at the fair market rent of $2000.

If they do, then you can likely find another tenant for that amount fairly easily, as I would assume the entire town's taxes are up- so if someone really wanted to be in town, that price is the new normal.If your taxes increased that substantially in a C neighborhood, your tenants would way more likely give push back for that type of increase- even though you're not being greedy, you're just imposing the same raise you were given.Often the buyer who had the "well, the numbers are better" mentality is only looking at year 1. 

Adhere to the Fair Housing Act and ensure that all applicants are treated equally.

After analyzing the potential ROI, we negotiated a fair price of $58,500, ensuring room for renovation costs and profit.

Offering 50% of the cleaning fee for cancellations within 48 hours seems like a fair middle ground.You might want to set up a clear policy with her going forward so everyone’s on the same page for situations like this.

If indeed a loss is taken on this which it sounds like is a fair possibility then if the agent was representing you the agents E and O will/could kick in and that's where you might get some financial relief.

Framing your position as fair such as explaining the difficulty of finding renters during off-peak months - might help maintain a positive relationship and reduce risks of property damage.Prepare for What’s NextEven if the tenant moves out early, ensure you’re protected.