My concern is someone who does not understand Chicago rules and regulations on units, airbnbs or the AUD profess in Chicago will direct you on these topics.

Another very dumb regulation is if someone switch jobs internally inside company, these circumstances makes them as they have no W2 as lender wants last two years with stable position.So again, here Credit union lender can give conventional rate that's very enticing by giving exception.

All the rules and regulations make it more expensive . 

Whatever it may be, establish the purpose of it.3) Do a study of what you're trying to get into and most importantly trying to avoid.

STR's probably take more effort than investors expect, but they are a proven and generally less available (due to regulation) asset class. - Do you data research.

You can figure that out by reaching out and talking with the municipality and/or reading their regulations for yourself.

Here are some steps you can take to get started:Establish Your Goals: Establish your financial and long-term goals while investing in real estate.

No matter how good your systems are you will likely end up in that city a few times per year at least, especially in the early years.With that being said, once you have your core team established in long-distance investing, it becomes much easier and problems equal google searches for vendors, phone calls and book keeping in your life (project management) vs. swinging the hammer or fixing a toilet yourself because you're forced to put those systems in place.I live in a similarly expensive city and would honestly be stoked to find a duplex in Denver for $600K!

But...If the average renter is being left behind, if their income can't stay in line with the cost of living, I fear it will lead to a larger crisis and continued intervention/regulation by government.  

Do you know the regulation for Florence?