We are actually trying to matket to this situation in our market tonhelp navigate all these questions

Can the regulations be navigated if the cash flow is there?

Let me know and I can provide some resources that can help you navigate the space. 

So far, so good - as we're working on two right now - but the main risk is just making sure you have the stomach and the chops to navigate these projects and at the pace your jurisdiction demands.I think your best bet is to just inquire with the sellers. 

Would love insight from anyone who navigated a similar issue and tips on how to pursue any of the following options.

Will definitely link up with you to talk through your situation more and navigate the tricky waters of Chicago!

Now, there are things you can do to navigate this.

I really need to start involving myself in the community as I don't have any other friends or family that are passionate about real-estate investing to discuss with. knowing someone that could watch over my shoulder as i navigate my first deal would be ideal but also a privilege.  

A knowledgeable and diligent property manager will protect your interests, reduce liability, and provide peace of mind.By following these strategies, you can navigate the changing landscape of the vacation rental market and maximize your profits.

I'm sure there are deals in those areas, but most properties will never cash flow because the sales prices are far too high.The regulations in California are arguably the most difficult to navigate in the entire country and it's easier to get burned by a bad tenant and lose your shorts.