I have tried to get quotes for these properties and I haven't found a company that is willing to insure me because I have open claims.

Quote from @Enrique Toledo-Perez: I'm a Realtor and I'm wanting to get into fix and flips by working with wholesalers and buying properties in neighborhoods with a good spread.

Hi David, you need a discounted propety, have you tried hyper focusing on off-market properties in your desired area.  

I just DM’ed you but I’ve househacked a handful of properties on the northwest side of Chicago.

Many months of costly vacancy, local market rent & resale deteriation, special assessments, property taxes and maintanance fees suggest a quick sale would have been the wise thing to do 2 years ago.

Are you doubling down on short-term rentals in tourist-heavy areas, pivoting to long-term rentals in growing suburban markets, diving into value-add multifamily properties, or exploring something completely different?

Be able to get into my first, 2nd or 3rd property?

I think a better option is to get a job in property management.

I have an opportunity to purchase an investment property that is NOT ON THE MARKET yet.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.