Looking to invest in Hawaii

[Joel Florian]

Summary: I want to become a real estate investor in Hawaii. And I have a bunch of questions. Any advice is appreciated but specific answers preferred.

1. Should I sell my $400k home in Alaska or try to rent it out?

2. Should I buy a 4-plex in Hawaii?

3. Should I buy a SFH in HI?

4. Should I rent for 6 months first?

5. How restrictive are building permits and inspections in HI?

6. Can I get financing since I have not had a steady job for the last 10 months? ( sold share of contracting business and have been consulting, doing home inspections, and rehabbing a flip)

7. Will the recent changes to AirBNB legislation in HI affect home prices in the next few years?

8. Should I even buy property on Oahu if I intend to move to the big island in 3 years?

9. Are there deals in central oahu I could get for less than $500 k cash?

10. Should I use a realtor? If so, please recommend one who likes biggerpockets.

11. Should I apply to become an appraiser in HI to learn more about the market?

12. Should I sell my tools and furniture and buy replacements in HI, or ship everything over?

13. If a house is listed as a "tear-down", how hard is it to get a permit to rehab it?

14. What is the most economical solution to extensive termite damage? Epoxy injection?

I have been a contractor in Alaska for 20 years. I have done 6 live in flips and just completed my first investment flip. I just found biggerpockets and listened to about half the podcasts. I think I've finally found my calling: real estate investing.

I just accepted a position on Schofield Barracks which is approximately in the middle of Oahu with the nearest towns being Wahiawa and Mililani.