At today's rates I'm not sure it would cashflow by the time you add taxes, insurance, r&m reserves, etc.The average rate today on a 30-Year fixed is 7.38%. 

When I first considered buying in the US I considered North Chicago as I know and like it but I'm aware of the high property taxes and question the longevity of the market there with a declining population and all that.I live overseas currently so any purchase will be remote for me and I will get it managed, I may never even see the place so I'm quite open to where I could buy.I wanted some thoughts on the best places to invest?

My wife is currently studying for her real estate license, so we can perform a cost segregation study on the property when we buy one to reduce our tax burden for 2024.

By building a seller credit into your offer, the seller can pay for ALL of your closing costs and prepaids, and you will get your earnest money back, plus any property tax proration credit as applicable.

Because of the protections an LLC offers in this space, I'd simply say my non-expert opinion would be to spend a little extra to make a separate LLC for this new home, for the legal protections & to make your taxes less of a headache for you.

I would recommend you read the book 'ninja selling,' as it provides you with a solid plan and schedule filled with action items to follow and execute to get results (if you follow it) And its not cringey, salesman strategies.

Needless to say, the tenants are scheduled to move out Apr30th.

Feel free to DM me if you want to schedule a chat.

We also need to communicate with our property management clients and service providers to schedule cleaners and handymen. 

If I use reward points for the flight/hotel/rental car, am I able to apply the value of those points to my taxes for the travel?