That should see me sailing into retirement with a bucketload of tax free $$$

hen you would be kicking yourself in the *** over that. you can't let what if's get to you. what if columbus never set sail?

Otherwise seems to be smooth sailing.

You'll find out how young 69 seems when you're sailing toward 60.

But to go further in the analogy, have you ever seen one man sail a ship and get very far?

By the time a market is hot enough that everyone is talking about flipping properties the ship in that market has already sailed. 

Even if your Boat is airtight, if the economic tide goes out, it will fall with the tide and you may not be able to sail away.It seems that Peter M. indicates that your chosen area has sound economics.So again, the risk tolerance of your circumstances may be above others who refuses to even consider things like saving your rent if you buy rather than paying much more if you didn't buy or even refuse to take any negative cash flow situations, but it is well within my risk tolerance levels.In fact, I don't even consider it a risk since there is a profit from the most pessimistic IRR calculations and the economics looks good for the future.Had I been had less Risk Tolerance, there would be no way I would have build a Real Estate Portfolio over the 21 years I have been Investing in NYC.

But I hope it will be smoother sailing from here for you on that one.Thanks!

Other than that it has been smooth sailing!  

Martin, I'm a bit of a boatie, suggest you reconsider renting any decent yacht, renters don't generally take care of them and you'll get those dreaming of the liveaborad lifestyle who find out shortly they aren't as salty as the thought they were.....high vacancy.Now, you can get a tub about 30 to 40' that shouldn't go out past the dock for dirt cheap, 5K for example, redo the inside more for living at anchor than sailing and you might have something, stay away from wood boats if you aren't handy below deck.