Additionally, have a clear budget, factoring in potential repair costs, and ensure you understand the rules about earnest money deposits and closing deadlines.LLC for Real Estate Investing: Forming an LLC for rental properties can offer liability protection and may provide tax advantages, though the tax benefits are non-existence for rentals.

Perhaps you could consider hard money in addition to private money?

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Additionally, working in a small-town market taught us how to effectively price properties for faster sales without compromising profit.

@Kenzer Hodgson For your STR, an umbrella policy can provide liability coverage, but an LLC offers additional asset protection by separating your personal and business assets, which can be valuable in case of lawsuits or audits.

I’m involved in a private LLC that owns land in which we are asked to provide additional $ for property taxes every year.  

If you used a loan to rehab your property and find yourself in a difficult position, doing a straight refi (just paying off the old mortgage) will be easier than trying to pay off the original loan and take additional cash out.

Quote from @Drew Sygit:My apologies w/my earlier post (below), I was on my phone and not laptop so it wasn't tagging.I will if I may add some additional thoughts...1) The appraisals I've seen in these markets are no where near Zillow estimates. 

So I disputed the additional charge. 

With some additions, this would qualify for the OMG category, but I think they didn't have that category back then when it was on the market.