So interestingly enough, when I went through training for property maintenance, we defined stipulations of normal wear and tear over 18 months, any residence less than that would be charged for carpet cleaning and minor damages like dings/dents that required more work than paint/spackle.

There should be a special stipulation along the lines of "All parties agree that tenant will provide time within 3 days of binding agreement for buyer and licensed inspector to access the inside of the property."

The phrase "this is a business" and "training your tenant" come up alot in discussions like this.There is a distinction between what that means said to a tenant and what that means when said to a business partner or peer.You want your tenant to understand that phrase to mean they should pay what is due, when it is due or suffer the consequences stipulated in the contract.

Do you stipulate the month to month rent amount in the lease?  

Like charge them as per the lease that stipulates they need to get insurance.

My leases are drawn up by an attorney, where those policies, ie, smoking, pets, etc, would be stipulated.

They signed a stipulation to leave on certain date or they pay the court fee but they never returned the key nor left on that certain date.

You can probably have the lease stipulate an exorbitant increase when a person or pet not already on the lease moves in even while at the same time disallowing a 5th unrelated person -all lessees being joint and severably liable.This will create a large financial disincentive to violating the lease (and the law) while also giving you recourse should it occur.

In both cases, sending a letter saying that if it wasn't resolved in X amout of time, legal action would be taken, solved the problem.It probalby didn't hurt that I wrote a CC on the bottom letter to a family member that is an attorney.Many states/cities have special regulations stipulating that landlords improperly withholding deposits are libable for multiple times the money withheld. 

I checked my current lease and realized I need to edit for more specific (blunt) language to stipulate they must carry renter’s insurance with liability.And to ensure the policy stays in effect, the agent suggests that I require the tenant to list me as an "additional interested party".