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?

If they do, your best bet is a local community bank that funds these types of properties.Another option is a private lender but that money will be pretty expensive, as mentioned 10%  + 

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.

Right now, I’m in full research and networking mode—learning about Milwaukee’s neighborhoods, connecting with local investors, and exploring my first investment.

You can work with a local credit union that does HELOCs, Home Equity Lines of Credit or Loans, on investment property.

I wonder if your local MLS provider has a list of MLS_only brokers in their system?

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. 

Wrapping 3 properties into one blanket loan shouldn't be a problem, save these are sitting on any sizeable acreage.You might get lucky and find a unicorn local bank or credit union that would consider that kind of leverage, but I would say overall, those terms are very unrealistic.Cheers!

@Audrey Sommer I prefer investing in my local market (Snohomish County).

I am new to real estate investing and looking to connect with any local investor.