Try it out first test out whether or not you two are a good fit before building a massive portfolio together.Create an operating agreement for your LLC, and create a partnership agreement, defining roles and expectations.

I'm currently planning to purchase a commercial multifamily building in Chicago with the proceeds of a 1031 exchange.

I'm especially interested in hearing about how you've made a PMS geared more toward STRs work with MTR billing and leasing.I do remote operations support for an MTR/LTR company in Denver and am assisting with our tech stack build out. 

I've had smooth loans close with Kiavi and I've had rough ones, same with Roc.When Loans start to be troublesome:1) The borrowing entity docs are a mess2) The appraisal numbers are lower than expected3) Messy background reports4) Loans happening in an environment where market/rate fluctuating unpredictably 5) Your loan officer and their team are poor at their job6) Title issues that depend on county docs, that can be slow and painfulThere's more but it's Friday and I'm tired....

So any extra pointers or tips , books, would be great guys I would love to connect and build relationships!

I know a lender that can help with both states that does investment lending for very cheap, it would be worth a connection as you look to build out your team no matter what you decide.

Wishing you the best in continuing to build out your portfolio. 

My goals are to start building an investment portfolio of professionally managed (I could tell you all the reasons I will not do it myself) multi-family properties and, in time, develop a property in the Northwoods (Wisconsin/UP).

What is status of capex on the building?

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.