Looks like Gustav may be Katrina part II right after it shuts down the Gulf oil rigs.

Luckily, I fell into an awesome job working for the nations largest producer of oil and gas where I make a decent buck.

The truth is that the success of some businesses is directly tied to its geographic location, i.e. salmon fishing, ice cream stands, mountain guiding and landlording.Yeah, it's a lot easier to do "out of state" rental when out of state is closer than your commute for work.

The two boilers together use more oil than one single boiler heating the whole building would cost. 

I understand theres bigger fish to fry in the real estate game but I want to be proactive. 

Consider too that we have unique risks (i.e. the state of our current budget and our dependence on oil.)  

Interior1st and 2nd Floor tenants have oil heat (they pay for heat themselves), 3rd floor is electric heat (tenant paid as well).

But yes if most insurance is water, then Florida is oil.

I allowed two pets at one of my properties and they ended up with 4 dogs, 3 cats and 4 huge fish tanks.

House hacking a 4-plex in Anchorage will not generate the returns you need to go spend all of your time fishing in Homer... but living in Homer and doing a STR in your guest cabin would mean that you are already where you want to be as soon as you clock out.House-hacking, AirBnB, tele-working... these things are all just tools to use to build the lifestyle you want.