And if the vacation rental is purchased under an entity, and all the expenses are paid automatically, and you set it all up so that monthly business transactions happen with out your involvment, you have and almost fully automated rental property maintained from a laptop via email and calendar. 

if values drop so will taxes, and you can deduct based on loss value, your rents will maintain with very minimal hit so hacking a hold is as strong of performance as you can get id look at cashflow over appreciation as you could essentially live for free if you do it correctly

No one has mentioned the time time and effort it takes to  find and maintain the property.  

Also keep in mind that license and membership in the MLS are not cheap to maintain, so it will actually push you to go out and make some sale or it will cost you moneyWelcome to BP!

I think you need to avoid placing the signs in the "right of way," as opposed to private property (possibly minimally maintained) that happens to be near a street.

What you have sounds like it is probably in the ball park of a property that is being maintained and you weren't given some rosy low figures on expenses.A good real estate professional can help you in a lot of ways and as an investor who is ready willing and able to buy, you can certainly help them. 

If I sell to an owner-occupant will the current lease be cancelled or do I have to honor the lease by transferring to a new owner or maintaining ownership?

Build and maintain a great credit score. 

I'm just trying to determine how much more is reasonable while maintaining the upside of the investment.Overall, I want my investments to cash flow but also have appreciation potential and appeal to future retail buyers.  

I have no employees to baby sit, no perishable inventory to move, no franchise fees to pay, and no store to maintain.