We are seeing a lot of investors have success with this strategy with plans to hold the properties they are rehabbing as rentals for several years before selling.

I position my inspections as 'planning for future repairs/improvements' which mitigates that whole 'he's here to get my security deposit' mindset.And, I would rather have the tenant with me than to have him later claim that something was broken during the inspection.  

What’s your contingency plan if costs overrun?

Most bookkeepers won’t work in it if you plan to outsource it in the future.

I had been dealing with them for several months due to the development of plans for a property I own.

So this involves hiring an architect draw up plans ($1,000 - 3,000 if I had to guess).  

Used houses in the area sell anywhere from $75-125 a square foot.These are long term rentals that I do not plan to sell.I am reading the Rental Property Investing book and implementing the method that focuses on cash flow and that strategy states you need to have $300 cash flow per month, per property.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

They can offer valuable insights into the local market, potential rental yields, and specific considerations for a rehab project like the one you're planning.

Tax planning is the key!