Self managing a property is challenging but educational.

2) When this becomes a LTR could your brother handle most/all of the property management to help bring this closer to 50/50? 

.- Seeking properties that can generate $2K+ a month in combined rent after factoring in property management, insurance, and property tax expenses.Seeking Advice:- Would purchasing two houses in the Midwest to achieve $2K+ cash flow per month be a sound strategy, or do you recommend alternative approaches?

Hey Chad - my office manager deals with this but we are not big fans of Airbnb.

It's crucial to ensure that the terms are manageable and that this approach doesn't jeopardize your financial recovery plan.2.

The tax deferral from a cost segregation study is a very powerful and strategic tool to utilize in a wealth management plan for your estate.Enhancement of Property ValueReal estate property that has had a cost segregation study performed on it is more appealing to buyers and investors as there is potential for a continuation of tax savings.

Did you find a good property manager in the area? 

@Devanand Ramachandran It sounds like you should hire a local property management company that specializes in the area and property type.  

One thing I did while at college was help manage student properties, and I found it to be quite profitable.

For long term I have less to manage but at the nightly rate and high occupancy the numbers sound way better.