Looks like a lot of us in here have a lot in common. I was born and raised in San Diego, lived in the Big Apple for over 10 years and my relatives have lived in Ft. Lauderdale for years, so I have spent a lot of time out there. While thankful for these wonderful experiences, there is no place I'd rather call home than San Diego.
As for Trudi's support for a place downtown, I can tell you that I represented a couple who live in North County Inland, but wanted a "stay-cation" place. They ended up with a place in the Marina District and couldn't be happier. It is easy to maintain, no yard work, close to shopping and restaurants, views to die for, and just a general buzz around there you can't find in the "burbs". The one downside I see, of course, is the relatively high monthly fees.
Now, specifically addressing your question, I'd figure out what your true passions in life are and that should directly affect your living situation. No matter what, I'd suspect that baby boomers want things to be easier as they add years to their life: no stairs, limited yard maintenance, smaller/easily manageable properties, ease of access to airports for those looking to travel, et.al.
I look forward to that day, but in the meantime, I'm going to keep living the dream in America's Finest City.
All the best in whatever it is you end up doing!
Chad Basinger, REALTORÂ®, CPA, CFPÂ®