Assuming my converting the use of the property (from owner-occupied to vacation rental, or from traditional rental to vacation rental) is the highest and best use of the property, and assuming there aren't may people aggressively doing this in my target area, many properties are not rationally priced to market (short-term) rents, but rather far below it in many cases.   

-Aim to be reasonable with your finances, not completely rational.

Rationally it'd make sense for me to pay 12% or more all day long for the slice from 70/75% to 90%+ and my blended cost still comes in lower than 9.5%.

Rent pro-ration should be handled by the title company, and future rent payment should have been communicated to tenants immediately upon taking ownership.

She has been smoking in the garage with the door up about a foot with the rational that the garage is not part of the house, which I told her it most certainly is. 

Try to separate rational from irrational fear and make calculated moves.

The thing you need to understand about mentally unstable people is they don't react rationally.

If your equity to value ration drops below 5 to 1, does that mean it's time to either cash out or sell to trade up?  

Tenant then told me that he "freaked out" about the bedbugs before and that he knew it was not a rational reaction.

The tenants knew I had done the job and never saw a bill, never even talked about how much it was, but fear isn't rational and fear of raised rent, unexpected bills, and/or eviction is a tough nut to crack when most of my tenants have had terrible landlords.