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.  

It really delays my entire plans.

Planning to invest in Research triangle are of NC for rental.3.

That could be your PM company if you plan to hire one. 

What’s your contingency plan if costs overrun?

If you're working on other projects during that time, it could create an issue, as it would for any employer.Why not be upfront with your boss and let them know you're planning to get your real estate license?

Even if the data is from 2022 let's say, its good enough for planning. 

The planning process can take a very long time!

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

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.