I know the larger/commercial property managers play this game of overcharging based on a "comfort fee" and have the volume to back up this strategy. 

Obviously we are new to the game so we are learning as we go. 

You should gather professional opinions from real estate agent(s) and an appraiser – these are the people with their feet on the ground and their heads in the game.

@Patrick Clark I would start by installing a video doorbell on your STR.

As for a revised offer, it’s a game of chicken....maybe they have better offers, maybe not.

Get a report if there is one Change the locks Repair any damage If it’s really bad call your insurer As mentioned this is a common game loser tenants play and often it’s a lie to cover up something

You will find a ton of useful information to help you with your foray into real estate investing.See here for the Guides:  BP GuidesSee here for the FREE video series:  The Financial Independence BlueprintSee here for the blog:  The BiggerPockets BlogSearch MeetUp.com for local meetups.And check out the New Orleans Real Estate Investors Association (NOREIA)Best of luck to you!

Anyhow, I'm very eager to get into the game and to start my journey to have some passive income for more financial security.

After this we spoke everyday making plans for a national company, creating content for videos and teaching others to do real estate investing.Please see where he indicates this in his email (attached)- "The reason I gambled with my time with you is I thought both of us could build a company together regarding lease options and land contracts in the midwest where these seller financing tools are common place."

I dont understand how being agressive and confrontational at this point in the game will help you.