My goal from this site is to get the education and connections/networking/friendships to help with our goal to be early retired, build/preserve our wealth, and a great happy life for my families future.

I was happy to see her leave, and she was happy to leave.There are certain damages to my property that I did not charge her for, and in hindsight I see that it was a pathetic attempt to win her friendship.

I am going to re establish my friendships with them by being active in their lives again and not be some old memory from years ago.

Fifth, what if I lost my job,  what if we lost our friendship and all what if scenarios. 

See BP Podcast 229 for more information.If I were in your shoes, and depending upon how good the friendship was, I would ask her for a portion of the profits she's made thus far, since you gave her a "friend's rate" on the rental and she's technically violating the lease, it's only fair.However, since you think she's not going to be honest about what profit she's made, I would assume you really aren't very good friends, just very old acquaintances.Regardless, I would terminate her lease at your earliest opportunity and begin short term renting it yourself.

A small one, (one that won't devastate our friendship if things don't go well). 

It's a small initial cost $5k I'm not sure it's allot to loose the place will cash flow at close to $2k a month once rented so worst case scenario I make my money back once or twice and then loose a friendship. 

If she comes to me and says she needs $20 to purchase more thread to make friendship bracelets I don’t immediately say no.

We would love to connect with anyone with local market experience and develop a mutually beneficial friendship. 

Living beside our current tenants for 2 years we have developed a friendship.