If you're looking to run numbers and get an idea of what this investment looks like I'd be happy to sit down with you and get it done via Zoom or in-person. 

I am interested in buying a condo or house near a New England ski resort, with the plan to rent it most of the time and while keeping a few weekends open each year for personal use. 

We run the credit report and background of the personal guarantor.

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.