Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

As stated by one of the respondents, this is a valuable experience for future investments.

Typically speaking, individuals living on either the West Coast or East Coast experience significantly higher home values which makes investing in rental real estate properties more difficult.

I have some real estate experience as a commercial real estate agent for the last few years.

Have been talking about getting into real estate investing for the last 2-3 years and finally pulled the trigger on a 3 unit house hack in Soulard that will be closing later this month and will be self-managing the property.I'm trying to network a bit with other investors, build a solid team of contractors / handymen, and set my systems up in way to scale, but also so my tenants have a good experience.

From my experience working with over 400 investors, I’d recommend starting with house hacking—ideally a fourplex if you find a good deal, but a duplex works too.

If the price was right on Turn-key maybe, but probably more of the fixer-upper that can be leveraged later on for additional property or sold for a nice profit. 

We aren't that big as we only have 5 properties/7 doors but it has been a great experience for us and we aren't looking back. 

Part of considering acquiring a property should include additional possibilities.

When you have the confidence & experience branch out and do one yourself.