What would help is if you had a partner or family member with better credit who would be willing to give a personal guarantee alongside you.

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.

Personally I use apartments.com.

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.

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

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.

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

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