Good suggestions. I have many of these. One word about the “app” idea. I had a great idea related to personal taxes that I tried to get off the ground with my accountant as a partner. I would say it’s difficult to do this unless you have a coder on your team. Hiring someone is not really viable financially unless the app is simple. When we finally got the quote for a coder to write what we wanted (and after doing lots of mock ups ourselves and getting a demo for investors) the estimate was about 750k just to really get started.

What a great plan to keep your condo empty of tenants but full of furniture! You will have so many options for family related use in the future: 1) hosting out of town family visitors long or short term, 2) relocating parents to live close by if the need be (assuming you don’t relocate to Hawaii), and 3) having a place for your offspring to live semi-independently. You can probably think of many other options also. At your income level (passive and active) who needs the increased tax liability and headaches / hassles / work effort required to generate a positive cash flow? Better to spend that life energy playing in the snow with your son!

Great diversification of passive income. I’m holding off on adding to passive income streams right now because I’ve still got a full time job and am already paying more than enough in taxes. It seems like a good strategy to focus on mortgage pay down and capital improvements to my existing rental property, and buying more growth stocks, then wait until after retirement or semiretirement to move things around with the goal of generating more passive income.
However, until we get another reset in valuations (I’m calculating a 40% to 50% correction is justified ), I’ve moved largely to the sidelines. Beginning in July 2013, I began slowly reducing equity exposure and am now sitting firm at 40% with the balance in various forms of 5 yr cd’s and short duration bonds. This is down from over 60% when I ramped up to take advantage of the March 2009 lows.
It is hard to do both but you’re not supposed to. You’re supposed to get your safety net down THEN try to do high wire acrobatics above it – not set up the two at the same time. So get retirement and your emergency fund squared away, then consider the stock market (taxable) and real estate. There’s no rush! Don’t let others dictate your future because they don’t have the same priorities as you. 🙂
There are many people who get paid vast amounts of money to become the CEO of a company, play professional sports, or star in a movie. Earning a high active income is often a lot of hard work and requires a dedication beyond most of us. It’s also limited because no matter how much money you get paid you still need to show up to work to earn your money.