Make sure you’re buying in solid cities or neighborhoods that will continue to attract renters.

I would highly recommend you sell and do a 1031 exchange into something that will produce income, like a rental property.

The additional income from STR could justify the renovation costs, but it requires active management and market awareness.LTR or Break-Even Strategy: Renting long-term might simplify things, but if it only breaks even, you’re right to consider if appreciation is enough motivation to hold.DIY Basement: DIYing the basement could increase STR appeal without the full $50K outlay, especially if extra space attracts more bookings.

Last year, the city required a bank statement, which was not overly difficult for me to produce; however, this year the city of Chicago required either a homeowners exemption or a state license showing the exact address and unit for the listed AirBnB. 

We will lose out on $100k but get our cash out and the new investor will clear $100k by sitting on a deal for a year (while collecting rents).Does this seem feasible or something that would be attractive to an investor?

This becomes EQUITY, which can be leveraged 4 to 1 to purchase income producing property.4.

This influx is largely driven by young professionals and families attracted to the city's burgeoning tech scene and quality of life.

I personally don't like wordpress sites since they attract a lot of spam.

**Mobile Optimization**: Ensure it’s mobile-friendly, as many users browse listings on phones.Some real estate agents or agencies use tools like LeadPages or Instapage to create attractive, lead-capturing single listing pages quickly.

Many so-called "income properties" don't produce nearly the kinds of returns we see advertised on the internet.