In Oceanside, New non-hosted STRs are prohibited outside of the Coastal Zone as of February 10, 2024.Most HOA's do not allow rentals less than 30 days so that is likely not an option unless you find a couple of places on the water that allow it but usually tough to find below $1M. 

Off-market property is the best option for fix and flip, but since you are planning to live and flip, some on-market properties would also work.

However, in the last couple of years, GLVAR modified their PM agreement to include an option for PMs to collect fees while the property is vacant.  

There is risk in both options & as an investor you need to weigh those risks & stand firm on whatever you decide. 

The house will need a new fence soon, so I'll have to factor that into the scenario.I'm not sure which choice is the best option for me.

From 9:45 to 20:30 walks through a summary of the proposal as well as options that the board has on the table.  

Another option would be working with private lenders to see if they're open to your idea should you need additional funding. 

Could be an option in your area.  

Hi Chris, there are several options you could consider, but it would all be based on your risk tolerance. 

Hey James,Ah, I see where you're coming from—given the Chicago winter, cutting off electric isn’t really an option without risking serious damage like frozen pipes.