Ask specifically what is needed to comply. 

It can be done but each situation is specific and would be underwritten to see the risk and what the exit strategy is. thats the key with shorter term loans - understanding what the borrowers exit is.

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.

These can be great for making initial connections and learning about specific markets.Since you're thinking long-term, consider spending some time in your target markets to build relationships with agents, property managers, and contractors.

Short Picture: Instead of dumping 300K out of a brokerage account all at once, how about you find another investment you are comfortable with, multifamily specifically, and only withdraw the needed funds for the down payment on it from your brokerage account. 

I think they just see the lower rent and run with it in that specific situation.

Usually, by the second month, you are figuring out how to evict.Sometimes we have a specific unit that has been on the market a long time. 

I know I already mentioned this, but @Mordy Chaimovitz...If you can get by with lower cash flow and invest for the long-term generational wealth (aka appreciation) in nice neighborhoods, that is the way to go, but it's tough to get by at times -- at least it is for me.Just know everyone's situation is different, and you should do what is best for your specific circumstances!

As for Alexandria specifically in terms of regulations don't take advice from a public forum - look up the laws yourself and make sure you understand them.

you'll probably get a good response, because it's a narrow, specific question.