Some of the coastal areas have seen substantial damage 5 times over the past 20 years.

I have gained substantial equity but don't want to pay capital gains and have been in the home for a short time (about a year).

The permitting timeline has improved substantially in recent months, both Planning and DBI have introduced new procedures.

These are the guys that spend lavishly well above their means and leech off their wife's more substantial income.

Unfortunately, due to Florida laws, substantial risk would be imposed on the seller if I were to do seller financing.

This seems like a solid start but when I looked back I think I stunted my initial growth rate substantially. 

The house raising or demolition is usually mandated when a house has substantial damage, or some similar term they use, which basically means over 50% damaged. 

Your education has also prepared you to analyze cycles and this point in the market is not an easy entry for passive investors not willing to be a small part of a much larger endeavor.In your case I'd be looking to real estate more as a tax hedge that will build substantial cash flow over time while delivering substantial depreciation and tax benefits from day one. 

(Well, it would be once the 6-plexes are fully rented.)Also consider what you have to maintain for each property:Office: 1 Roof6-plexes: 2 RoofsOffice: 4 HVAC units6-plexes: 12 furnaces + 12 AC window unitsOffice: 2 kitchenettes (Fridge, sink)6-plexes: 12 full kitchens (Above, plus range/oven, vent/hood, dishwasher, etc.)Office: 4 bathrooms6-plexes: 12 bathroomsA couple more confounding factors: The office building is built in 2005 and located in a suburb of a major metropolitan area currently experiencing substantial growth.

Although our portfolio is growing substantially and we've got solid income coming in, I'm not sure that it's quite at the point where it would stand alone on its own and command financing options (without my wife's W-2 income).