If you're putting in sweat equity/forced appreciation into the deal, you most likely will be fineIt may be worthwhile having it as an AirBnb after you move out to boost your cash flows if that is something you'd be interested in I bought my first SFH house hack even though it didn't cash flow fulled rented as-is.

But for Property Manager Ed, $220 is a nearly 20% boost to his income and is a significant motivator.

I don't see how any of that makes sense.Speaking of Prop 13, you will lock in a lower tax basis by purchasing at cyclical lows, which boosts your long term profitability as well as your immediate chances at cash flow.The sales commission for the $50,000 property would be $3,000 and as long as the property is greater than a 6 cap it will cover that in less a year.  

He's definitely going through some mental issue's and I feel bad for him but I need to take immediate action.He's now gone for 2 weeks, his unit is oddly cleaned up with furniture strategically placed to cover up certain holes in the walls.

Plus, they help with the hassle factor of coordinating everything and the mental load.

I don’t fully subscribe to everything he says, but he’s not wrong when it comes to the mentality behind what I’m saying.

The right to remediate is important when you have tenants with challenges (physical, mental or emotional) that interfere with their ability to maintain a clean unit

Buy and Hold mentality, while collecting returns.  

The first 30 days is critical as that is when you get the boost in search results from Airbnb and VRBO.

I am not sure how you market the property, if you market it as a short term rental and/or vacation rental but if you target vacationers maybe try notifying travel agents of the property as it may boost interest, they will generally (I believe) want some sort of kickback or concession if their clients rent the property but that is a small price to pay to have it rented instead of vacant.For vacationers:As for the reason for the late/last minute bookings, I think many people feel the later they wait the better deal they can find so they purposely wait knowing that in the event they don't find a cheaper rate they will still be able to secure a place so there is really nothing to lose for them, it's not like the price will go up the closer it gets to their arrival date.