I know I get really caught up in details, deals, etcetera, and need to take some time to relax occasionally.Thanks for the nice reminder.  

@Brigitte Via if it were $100k, form my experience and current market conditions:- $50k in diversified ETFs- $50k toward buying a STR in a vacation friendly holiday destination townAll the best!

Before a holiday weekend...

You had the July 4th weekend in there, kids are just out of school and families are starting holidays.

It is my belief that Miami will soon grow to be much like NY but with a more tropical and a bit more relaxing environment, hence why people are investing into it now.

Chartering a yacht is a superfluous activity by those looking for please and relaxation. 

(FYI - The rental market in DC ends about Thanksgiving and picks up in March so try to get in before holidays or look for a place to work in early Feb ahead of demand.)

My birthday is smack in the middle of the year, so I use that and the end-of-year holidays to sit down and ask myself those questions.As some folks have already mentioned, if you're putting 90% of your work into areas you don't enjoy, find a way to outsource that work and focus on what you do like.

From that point it is not a far reach to be potentially liable for any injuries he might get during the course of "working for you".I would highly suggest that you get him a nice birthday or holiday gift in the near future and just thank him for being a "good tenant".Good luck on what every you decide!

Holidays are always booked up quickly as well.5.