Plus a room in the basement i planned on making into a air bnb.

I am up in the air about renting it or selling it outright and using the funds to buy a few properties, including the ski resort condo with loans.

(took a few tries to spell that right)  I have always plowed my profits back into my business, but my business exploding is more like little puffs of air every other year or two hehe. 

I suspect Oahu to be a more difficult market to succeed in due to the sheer number of air bnb and hotels by comparison.

For years, spec developer Niami has teased “The One” — a 100,000-square-foot mega-mansion in Bel-Air that he hoped to sell for $500 million.

So attempting to hit 20% IRR on such deals at present, is most likely hot air.

I am retired Air Force myself and building a passive income stream for the time after your service ended is a great approach I wish I would have known about when I was still on active duty.Last point: I suggest taking advantage of your financing benefit as a military member.

We’re moving to a new house now and will do it all over again: increased insulation, tighter building envelope, more efficient appliances, electric radiant heat in the floors (way better than forced air anyway), and passive and active solar instead of gas.

Just plan for worst case scenario 1-2 years of mediocre STR bookings and if you can survive this you’ll probably do well.You’ve already down the best research you can do- Air DNA plus just looking at the calendars of current Air Bnb listings in your desired area. 

I'm looking to do a vapor barrier to reduce any potential moisture, Insects, raydon, just better over all air quality is what I'm going for.