I have a few Airbnbs and know what we execute on to stand out but it just seems like there's WAY too much competition and the juice might not be worth the squeeze.We're trying to be within 10 minutes from the beach and downtown, which is putting us at a price point around $600K for a prospect property, but even with those numbers at 20% down w/ taxes/insurance, it doesn't seem worth it with the surrounding competition.

It’s great to see how the right structure and quick execution can really pay off.If you haven’t already, it might be worth connecting with a tax advisor who specializes in real estate to help plan for the tax side of that profit.

(I'm open to buying outside of Baltimore)Executing the Flip Successfully:What’s the best way to go about completing a flip,  especially for someone doing their first one?

That's easier said than done, and you're only going to create that level of income if you execute and self manage well.If nothing lights you up, I'd invest in index funds and pull money out at a 5% withdrawal rate (gets you halfway to $40k), stay completely liquid, and have none of the hassle factor.

Hiring a full time Property Manager will likely make it difficult to execute the Short Term Rental Loophole, but many Property Managers offer consulting to allow you to fast track your learning curve on providing exceptional service.

In most cases, a credible JV person will only deal with people who have a proven track record, that they strongly believe can execute their part of the equation.

I know this was a huge mistake, and I haven't come here to have people say to not do that - I definitely know to not do that now based on this experience; it's been a very good lesson.The lease agreement says that the security deposit and the first month's rent were due at the time of the lease execution, so we immediately sent her invoices via our rental platform to pay; since she signed the lease via the platform she already had an account.

As @Collin Hays said brace for impact.Historically, during the last major shutdown under Obama, that was designed by the executive branch to hurt, I was active duty and saw it first hand. 

This is an executive home on a private airstrip, and my husband is a pilot, so hopefully it will be obvious that this is not a great rental and we plan to move in.  

Next step: get the HOA letter and a lender pre‑approval, then pick one priority to execute first.