He has a very good job and great credit but is young and immature so I kind of just want him to go away BUT hate the hassle of having to show the place again (40+ min drive from my house each way), run background checks, etc.What would you do in a situation like this?

Have you factored in holding costs (insurance, utilities, taxes) and selling costs (commission, tax/deed fees, etc)?

It only looks dumb when things are going well or in a highly stable environment.And I don't think your opportunity cost calculations factor in risk spread appropriately.

Just factor it into your numbers and if it doesn't pan out then move on to the next one.

Also, each area have varying standards on when a permit is necessary, so you'd have to factor that in too. 

Cost approach is a different subject matter and...I think the owners are factoring rehab into their asking price?  

The search algorithms differ for each platform, but for Airbnb the main factors include response time to inquiries, instant book turned on, pricing, and reviews.As others have mentioned, I would look into other platforms/websites that focus on corporate rentals.

Yes family and friends where our driving force to the areas we invested in.

Investors typically consider factors such as the size of the market a company is addressing and the track record of the management team.

So I just mailed him an introduction letter, and will drive down and visit him in person next week.