Moving to Hawaii From Chicago

[Ben I.]

Hi everyone. Posting here to see if I haven't thought of something. My family and I are moving to Oahu in a month. There I will be working as an engineer. Leaving behind in Chicago 2 properties; a two-flat and a three-flat. They are all going to be fully rented out and I don't plan on selling them. 80k of HELOC is available to me from one of them.

Once in Hawaii, I will not be able to invest in real estate locally due to the million dollar entry requirement for Oahu. I am considering a few options. 

-Buy back taxes in states where it makes sense (NC, FL & Texas)

-Buy condos in Chicago (pro: relative maintenance free)

-Partner up with a friend and BRRRR in Chicago

If you were me what would you do? We plan on being in Hawaii 10+ years. 

[Eric M.]

Originally posted by @Justin Kurpius:

@Jason Marcordes

My contractor’s real estate agent said the last three homes she sold were all people leaving state.

My water softener guy said he is seeing A LOT of the wealthy in the Barrington area leaving the state.

It’s not a good situation right now with no improvement from what I can see.

Good luck!

 Not saying all that anecdotal stuff we hear is not true but it is only a sliver of the story. 

Like who is buying the house? I just sold my house and am staying in the city. The people who bought it were executives from Belgium moving here. You can't just look at half the equation. 

Each of us has a very myopic view of what is happening that is colored by our own opinions. If we think Illinois or Chicago is going to ****, we talk to people about that and miraculously find other people who think the same. We pay attention to those news stories and the statistics which confirm our opinion.  If we think things are great, we happen to run into others who think they are great. We tend to see the construction, the activity, etc.

I just bought a particular model car for my kid. All the sudden I am seeing all kinds of the same cars on the road. Humans are confirmation bias machines.

For example, did you know that for 5 straight years, 2014-2018, Chicago was the number 1 city in the country for corporate relocations?

There are a couple of "think tank" type groups that are behind much of the "hype" about population loss. They are political groups who are against taxes. (illinoispolicy.org and macdonald hopkins) Taxes are easy to be against, but the political groups do exaggerate, cherry pick data and hype it to make their point. They are very effective.

Another example, amid all the population decline news, they almost never mention that they largest demographic leaving the state is retired people. Is it really so shocking that retired people move south? But as much as we love old people, they don't contribute a whole lot to the economy relatively speaking.

Ask a 25 year old and they know ALL KINDS of people who are moving here for jobs. Ask a 60 year old and they know ALL KINDS of people moving away to retire and stop shoveling snow.

Just a different perspective. Doom and gloom has been predicted since I moved here 30 years ago. It hasn't happened yet.