As far as meetups go, you can find a lot of local events posted here on BiggerPockets: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of Chicago meetups that I can share with you as well.

Zero in 2024 in Huntsville - which is precisely why we bought zero LTRs in 2024 locally (bought one out of state, and bought a local flip property and one small local commercial property - slowest year since I started REI in 2017). 

One needs to have outstanding local market knowledge to underwrite effectively. 

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

If you're focusing on rural properties, sometimes local community banks or credit unions are open to these types of deals.

Best bet is to try local and credit unions, possibly may have some programs for better rates.

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?

I highly recommend investing in a property management software, such as Hospitable, for syncing your calendar, automating messaging, and scheduling cleans, as well as a dynamic pricing tool, such as PriceLabs, for optimizing your pricing based on market demand, local events, and seasonality. 

There are some programs through local government systems where you may be able to receive a tax abatement or grant here in Michigan in an effort to help beautify a neighborhood.

To invest out of state successfully, focus on building a strong local team (agent, PM, contractors), automating deal analysis, and using contingencies to protect yourself.