My brokerage syndicates it to all the sites but zumper gets the most hits.

Hey Nate, it makes sense to continue building out your investment portfolio in Milwaukee, but if you're looking in the Midwest, I recommend you make sure you get very familiar with the market you're interested in and build your out-of-state team first such as an agent, property manager, lender, and contractors if you're planning on house flipping.I recommend checking out Long-Distance Real Estate Investing by David Greene, where he takes you through how to properly invest out-of-state. 

Hi I’m looking to start investing & would like some helpful tips/advise from any experienced investors.

STR I would highly recommend not to focus on as first investment: also there, my partner is a superhost and we have been managing Airbnb for years and the last year has been pretty funky: people tend to book last minute and you risk to be cash flow negative starting brand new.

Look for recommendations.

Bigger Pockets is a great place for education and networking and is full of great content.I recommend that you check out the following resources:1.

Recommendation: Contact a qualified professional.

Any tips for managing the complexities that come with wearing all those hats?

I highly doubt a day or two will cause that much of a damage.

I recommend my buyers take their tax return draft to their lender to discuss the pros and cons of taking certain deductions.