It all seems pretty feasible and attractive, but curious if there are many lenders or investors actively taking advantage of the program.   

Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

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

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

While there are many options on the market, targeting neighborhoods with consistent renter demand and investing in well-maintained properties will help you attract tenants more quickly and reduce vacancy risk.

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.

The property location, the condition, and the type of students that the property attracts would all go into that.

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.