For the next round of tenant applicants, I would carefully explain that there was recently a roach issue at the property and that roaches are common in the area, so they are not surprised when they do see one or want to immediately move out over it. 

Once you have known costs, you can go back to the seller and explain that anyone that buys that home will end up doing the same that you will be required to do as their conventional or govie lenders will stop the loan based on the appraiser identifying these as unpermitted additions.

Would y'all mind sharing some advice or explaining any downsides to this plan?

You would contact the escrow company to explain your situation and ask about this…or have your lawyer do it.

@Moaaz Malik investing in a market that doesn't fit your investment objective isn't risky.

Start by defining your goals and criteria and then identifying the markets that fit you're investment objectives.

Explaining where I want to go will help me at this point so please bear with me.

Meet with "Tenant 2" first and explain that you are owner occupying the property.

It's possible if you are doing that, your friend/agent got bored with trying to run down either lowball offers or continue to explain how hot the market is.

Call them up and explain you would like to learn from them.