Please let me know if you need more info to create a clearer picture.Thank you.That is actually a good question to get advice from a local estate attorney on.

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?

Currently, I’m in full research and networking mode—learning, looking to connect with local investors, and exploring my first investment.

Go to your local credit union. 

We've worked with local banks and been able to finance the three we own without any issues.I don't necessarily know if it's "beginner" investor friendly but you'll learn everything you need in the bootcamp which is the gold standardWe get loans with 3-7 year balloons and 25 year amortization typically

I am about ready to just manage myself from out of state and have a couple of local handymen help me out when things come up.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

There are many local real estate investor groups or associations.

I would connect with a local PM who has connections with the HUD programs so you can get the most accurate information and guidance in your market. 

Check out the Events and Meet Ups section for local events in your area.