I recently had a long-term (5.5 years) tenant move out.

@Kristin MathernI would pay it given no keys were provided, it wasn’t specifically addressed/mentioned in your lease, you were provided the opportunity to address/fix yourself with a 25-30 dollar replacement from Lowe’s/Home Depot, and lastly, it was an existing situation that could have been avoided/prevented at move in.

For instance, the term could be 3 years and add a clause that says they have to return the property to the condition it was in when they moved in, not just keep their deposit. 

Remember, confidence grows with each step, so take action and keep moving forward!

Troy helped me identify properties with strong short-term rental potential, and when we found this home in Palm Harbor, we moved quickly to make a competitive offer.

Tenants like to set up insurance, show proof to the Landlord, and then immediately cancel the policy after moving in.

We just gave our tenants notice that we are planning to move into the rental they are leasing from us.  

2.The best way to obtain the necessary permits and ensure compliance moving forward?

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.

Good morning @Joshua MartinGreat thing about a VA mortgage is you can do an IRRRL even after you have moved out of the property!