It is also better than what I would have received for a comparable lot in other locations. 

Then compare that with your normal 30-year fixed.

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.

Even if I have a claim every 10 years I will have saved $80k over that time period compared to the people who pay for better insurance.

Quote from @Danae Pitcher: How is everyone seeing the holiday bookings this year as compared to last year?  

Having that been said, the barriers to entry are very low, which makes it one of the easiest countries for anyone to start doing Airbnb, when compared with other countries.

@Jamie ParkerAppreciate the effort and plan you are taking - it part of every plan is to re evaluate to move forwardHow much time have you spent compared to how much have you made?

I had some luck in real estate groups and by sharing success stories, but the pace was slower compared to paid ads or SEO methods.One thing I recently explored was incorporating tools like those for Social Media Posts using AI.

As long as you stay invested and let your hard earned capital continue to grow, you can pick your spots when a real estate opportunity offers outsized returns comparatively to other investments. 

We do know the border had its issues, but currently illegal crossing are lower compared to when Trump left in office.