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.

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.

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?

Vacationers are starting to go back to hotels as Airbnb fees have increased and they don't want to deal with cleaning dishes on top of paying cleaning fees.We stayed in a nice vacation rental on the Oregon Coast and there was evidence that kids or homeless were hanging about when it was vacant.  

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

And a refinance will have fees attached to it which makes this even less attractive.3) Just because you are not a professional test doesn’t mean you can’t add value.

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.

Year-round road access can also vary, with some parcels only accessible seasonally.Market Trends: The Fairbanks real estate market is competitive, but when it comes to land it's not very competitive and the prices are still relatively affordable compared to other states, making it an attractive option for investors or builders.

The best way to have a reliable tenant in your property is to:Buy a property that attracts a tenant segment with a high concentration of reliable people.Work with a property manager who can consistently select reliable tenants.