Hey @Robin Gravlin - I am super sorry to hear about your struggle, but know WHEN you make it through this EVERYTHING gets easier.I have equally had a very challenging property ironically (@Jay Hinrichs) on the south side of Chicago. 

This challenge may cause you to take the path of least resistance and pursue a 2-4 unit with a residential mortgage.

It is the biggest cost/challenge for making rentals work in my opinion.  

However, annual rents for lease extensions grew by 4%, highlighting renters' preference to renew rather than enter the challenging homeownership market.Looking ahead, the multifamily sector presents a mixed landscape of opportunities and challenges.

As a resident of the Gulf Coast of Florida (Bradenton) we just witnessed the strength of Mother Nature with the most recent passing of Hurricane Helene in the Gulf.

As you may know being local, SB249 is the bill that came up as a defense against towns like North Conway trying to shut down STRs, but it ended up in zombie state due to the sheer nature of diametrically opposed views on the matter and Governor Sununu’s push to do better than what the bill ended up proposing.Some details here: https://legiscan.com/NH/bill/SB249/2022As with all areas in New England I encourage investors to start thinking of oversaturated STRs markets as expense offset versus cash flow properties.

So, trying to convince her to have a stranger share a bathroom might be the most challenging feat I've faced. 

Lake Coeur d'Alene is a natural deep water mountain lake with an average depth of 125 feet.

First flip maybe challenging and risky.

What are the biggest challenges you’ve faced with either strategy?