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

Typically you will close sooner than 30 days, but this way if there are any issues or anything that slows down the closing, you have some additional time to close still.

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

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and it's super landlord friendly (so you will never have to go through a 12 month eviction or anything close to that!).

@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.

So I disputed the additional charge. 

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.

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.

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

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.