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.

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.

Hello BP Community,As a person familiar with real estate investment, I am now trying out a new type of investment in travel.

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.

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

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

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

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.