I see them p*ssing away the money constantly on vacations and crap that is losing value. 

You just increased your net worth by almost 50k, get additional monthly cashflow while your tenants are paying your self eliminating debt down and you enjoy some nice tax benefits.

I really enjoy the science vs art part of it, seeing consumers improve over time, vs fall-back behavior.  

My goal here is to break even on cash flow the first 3-5 years, with gradual income increases, and enjoy owning a beautiful property in an amazing location, holding it while it increases in value, and any increase in income serves us well over the duration of our ownership.Your thoughts?

I'm sure I would enjoy the "job" of flying but at this point I'm just questioning my future and whether or not that would be a wise decision.  

You want to give him incentive to leave without trouble.I would call your lawyer and have them ready to serve notice to vacate if he is not gone on the last day of his lease.

The constable will be at their door and give them 5 minutes to vacate!

I enjoy many outdoor activities (running, biking, surfing, and skiing) as well as traveling.  

If you have to get three estimates for every thing you need done on 8 units plan on taking some vacation. 

slightly off topic . in Hawaii, while on vacation we heard some loud yelling and and what sounded like a lot of domestic violence happening - I went outside and was trying to determine the location of it and soon another guy joined me who had also heard it - we discovered the room it was coming from and both approached to ask if everything was ok - a big muscle bound guy answered the door sweating and breathing heavy - he said everything was ok and that him and his girl were just having a disagreement -when asked if she was OK - he said yes - then the guy that was with me asked she could please come  outside and confirm to us that she was OK - I was a little taken back by his boldness , but was glad he asked - so she came to the door and confirmed she was OK and didn't need any assistance.