She ended up living in my home rent-free for one month (also didn't pay her utility bills) before moving out as I gently told her she needed to move along.

Great, Great discussion.It's ALL ABOUT relationships, be it a banker, realtor, carpenter, etc.I love reading all the postings.Remember to be gentle; we all learn from each other, and our experiences.Us old timers were newbies at one time too!

Please be gentle on me.

explain that his rent is way under market and that you will be gently nudging in up over the next several years.  

If the unit is a rental and you don't want to spend the money to refinish the floors, sometimes you can get away with a buff and coat, depending on if any other contaminants have been sitting on the finish, such as floors being previously waxed or furniture polish that has remained on the floor when the previous owners were cleaning their furniture.

Just be gentle....

Then when "Billy" suggests getting on the roof you can gently remind him that getting on the roof is prohibited by the lease and while he would probably do a wonderful job you have to enforce the lease uniformly or risk a fair housing claim from the government.

You may or may not win this, be gentle but firm with your position when explaining it.The tenant that occupies the basement could be twisted a couple of ways.  

Simmer gently for 6 months (seasoning time in lender speak) 5. 

Just some gentle feedback.