However I ran a few quotes on Obie Insurance (geared specifically towards landlords) and for only the 4 houses I checked, I am saving 1,5k a year if I switch.

As a builder/investor myself some of your estimates seemed a little off to me, but those can be very market specific so its hard to say. 

Also, nightly stays should be adjusted based on your specific pricing strategy as well (e.g. longer stays further out, shorter as dates get closer or gaps exist).

Alternatively, once you have a full time job (or an employment contract), you should be able to qualify for a loan and utilize a Down Payment Assistance program.

Maybe pay a financial advisor for an hour of his time first in case there is an alternative that you have not seen yet?

Quote from @Emily Gowen: I only recommend investors sell when they can move the money to a better-performing investment or when the sale moves them closer to a specific goal.

Despite the inability to claim depreciation or avoid certain taxes, many investors appreciate the control an SDIRA offers, allowing them to invest directly in real estate and other alternative assets they are passionate about.I do not recommend buying tax-efficient assets like RE in the already tax-efficient IRAs.

Based on our experience, we’d be happy to connect and share insights into viable areas, property management options, and financing solutions tailored for cross-border investors like yourself.Cleveland is a fantastic market with solid cash-flow potential, but as with any investment, having the right team in place is key.Feel free to reach out if you’d like to connect further or discuss specifics—I’d be happy to help!

Quote from @Tanner King: Where are the best places or best ways to collect data on specific markets?

Group training sessions do not deal with specifics that lead to lawsuits.