Just want to make sure you linked the right person there?

If you have self employment or gig jobs you need 2022 and 2023 IRS taxes filed and all the pages/1099/w-2/LLC/Corp/personal and 2024 income.

I know personally when im looking for a place to stay if its a little more pricey my brain usualy jumps to "oh this place must be better than the others" since this is a heavy market for vacation rentals and not traveling professionals I could see that being a factor but it makes it very difficult to price and what price point to risk.

I've narrowed in on some areas I personally enjoy and at first glance seem like they would be good STR markets in the PNW where I live.

It can help safeguard your personal assets in the event of a lawsuit or liability claim that exceeds the coverage limits of your primary insurance policies.Tenant Acceptance Policy: Implementing a thorough tenant acceptance policy is crucial for selecting reliable tenants who are likely to pay rent on time, maintain the property, and adhere to lease terms.

If possible, consulting a local real estate agent or financial advisor can provide personalized advice based on the specific market conditions in Chicago.

I am going to message you my personal point of contact there :). 

It's a great place to network and connect with others in person.

These technologies are not just passing trends; they are the vanguard of a new era, swiftly outpacing the conventional workforce.The Rise of AI and Disruption ToolsThe real estate industry, once reliant on personal connections and local knowledge, is now being reshaped by AI.

For any new acquisitions though you’ll likely want to buy in a new LLC just to create some separation between your personal liability and your rental properties.